Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

A synthesis of the carbon skeleton of maoecrystal V.

ABSTRACT: An enantioselective synthesis of the maoecrystal V (1) carbon skeleton is described. The key transformations include arylation of a 1,3-dicarbonyl compound with a triarylbismuth(V) dichloride species, oxidative dearomatization of a phenol, and a subsequent intramolecular Diels-Alder reaction.

SUBMITTER: Krawczuk PJ

PROVIDER: S-EPMC2783297 | biostudies-literature | 2009 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

A synthesis of the carbon skeleton of maoecrystal V.

Krawczuk Paul J PJ Schöne Niklas N Baran Phil S PS

Organic letters 20091101 21

An enantioselective synthesis of the maoecrystal V (1) carbon skeleton is described. The key transformations include arylation of a 1,3-dicarbonyl compound with a triarylbismuth(V) dichloride species, oxidative dearomatization of a phenol, and a subsequent intramolecular Diels-Alder reaction. ...[more]

PMID: 19795876

Similar Datasets

Total synthesis of (±)-maoecrystal V.

Project description:The total synthesis of racemic maoecrystal V has been accomplished. Key steps include an intramolecular Diels-Alder cyclization to rapidly construct the core system from simple starting materials and the creation of the A-C ring trans-fusion through intramolecular delivery of a hydrogen to the hindered ?-face of the ring system.

| S-EPMC3512084 | biostudies-literature

Studies toward the synthesis of maoecrystal V.

Project description:An approach toward the synthesis of maoecrystal V is described. The synthetic strategy for this approach was designed to address unique challenges posed by the strained tetrahydrofuran ring at the center of the target structure.

| S-EPMC3373731 | biostudies-literature

11-Step Total Synthesis of (-)-Maoecrystal V.

Project description:An expedient, practical, and enantioselective route to the highly congested ent-kaurane diterpene maoecrystal V is presented. This route, which has been several years in the making, is loosely modeled after a key pinacol shift in the proposed biosynthesis. Only 11 steps, many of which are strategic in that they build key skeletal bonds and incorporate critical functionalities, are required to access (-)-maoecrystal V. Several unique and unexpected maneuvers are featured in this potentially scalable pathway. Reevaluation of the biological activity calls into question the initial exuberance surrounding this natural product.

| S-EPMC4974602 | biostudies-literature

A synthesis of the carbocyclic core of maoecrystal V.

Project description:An approach toward the synthesis of the complex polycyclic diterpene maoecrystal V (1) is described. Construction of the advanced tetracyclic core structure (i.e., 19) was achieved in 13 steps from 3,3-dimethylcyclohexanone (6) by employing a stereoselective Nazarov cyclization followed by a Diels-Alder reaction to forge the two contiguous quaternary stereocenters.

| S-EPMC2896894 | biostudies-literature

Enantioselective synthesis of (-)-maoecrystal V by enantiodetermining C-H functionalization.

Project description:The evolution of a program directed at the enantioselective total synthesis of maoecrystal V, a highly modified ent-kauranoid, is described. An early stage chiral auxiliary-directed asymmetric C-H functionalization for the construction of a key benzofuran intermediate enabled the first asymmetric synthesis of the natural enantiomer of maoecrystal V, confirming the assigned stereochemistry. A divergent course of the central intramolecular Diels-Alder reaction, which is dependent on the nature of the dienophile, initially led to the development of an unanticipated and previously unknown isomer of maoecrystal V, which we named maoecrystal ZG. In light of the reported selective and potent cytotoxic activity of maoecrystal V, the cytotoxic properties of maoecrystal ZG were also investigated.

| S-EPMC4291805 | biostudies-literature

Toward the total synthesis of maoecrystal V: an intramolecular Diels-Alder route to the maoecrystal V pentacyclic core with the appropriate relative stereochemistry.

Project description:A diastereoselective route to the maoecrystal V core compound (6) has been achieved. Key transformations include an intramolecular Diels-Alder cyclization and an exo-glycal epoxide rearrangement sequence.

| S-EPMC3079889 | biostudies-literature

Assembling the carbon skeleton of A-74528.

Project description:The 2'-phosphodiesterase inhibitor A-74528, which combines an intriguing biosynthesis with unusual biological activity, is one of the most complex type II polyketides. As a synthetic target, it represents a significant challenge due to its size but also due to a unique carbon skeleton that features a hexacarbocyclic core with an appended pyrone. Here we report our efforts toward the synthesis of A-74528, which culminated in the construction of the full carbon skeleton and the correct installation of all but one stereocenter. Our strategy employs a molybdenum-catalyzed branched allylation to establish the central quaternary carbon and relies on establishing the remaining stereocenters in a substrate-controlled manner. Carbocycles were established using a spiro epoxide annulation, a 1,3-dipolar cycloaddition, followed by an aldol condensation, and a gold-catalyzed hydroarylation. The pyrone was appended to an aldehyde branching off the quaternary stereocenter by a one-carbon homologation and Mukaiyama aldol addition.

| S-EPMC9297437 | biostudies-literature

Efficient construction of the securine A carbon skeleton.

Project description:Securamine A is a structurally intriguing alkaloid possessing a pyrroloindole core joined via a modified isoprene subunit to a functionalized imidazole ring. Recent synthetic efforts in this laboratory have resulted in the efficient construction of key lactone 36, which undergoes tandem azide reduction/ring expansion to macrolactam 37. Macrolactam 37 possesses the complete macrocyclic core of securamine A.

| S-EPMC514433 | biostudies-other

Enantioselective synthesis of the lomaiviticin aglycon full carbon skeleton reveals remarkable remote substituent effects during the dimerization event.

Project description: Not available

| S-EPMC3152949 | biostudies-literature

Synthetic Studies towards Maoecrystal V.

Project description:The investigation of an intramolecular Diels-Alder reaction, en route to a projected total synthesis of maoecrystal V, is described.

| S-EPMC2822274 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data