Unknown

Dataset Information

0

An efficient, second-generation synthesis of the signature dioxabicyclo[3.2.1]octane core of (+)-sorangicin A and elaboration of the (Z,Z,E)-triene acid system.


ABSTRACT: An efficient, second-generation synthesis of the signature dioxabicyclo[3.2.1]octane core of (+)-sorangicin A (1), in conjunction with an effective, stereocontrolled protocol to arrive at the requisite (Z,Z,E)-triene acid system has been developed. Highlights of the core construction entail a three-component union, a KHMDS-promoted epoxide ring formation-ring opening cascade, a Takai olefination, and a chemoselective Sharpless dihydroxylation. Assembly of the triene acid system was then achieved via Stille cross-coupling with the ethyl ester of (Z,Z)-5-tributylstannyl-2,4-pentadienoic acid, followed by mild hydrolysis preserving the triene configuration.

SUBMITTER: Smith AB 

PROVIDER: S-EPMC2880660 | biostudies-literature | 2009 Mar

REPOSITORIES: biostudies-literature

altmetric image

Publications

An efficient, second-generation synthesis of the signature dioxabicyclo[3.2.1]octane core of (+)-sorangicin A and elaboration of the (Z,Z,E)-triene acid system.

Smith Amos B AB   Dong Shuzhi S  

Organic letters 20090301 5


An efficient, second-generation synthesis of the signature dioxabicyclo[3.2.1]octane core of (+)-sorangicin A (1), in conjunction with an effective, stereocontrolled protocol to arrive at the requisite (Z,Z,E)-triene acid system has been developed. Highlights of the core construction entail a three-component union, a KHMDS-promoted epoxide ring formation-ring opening cascade, a Takai olefination, and a chemoselective Sharpless dihydroxylation. Assembly of the triene acid system was then achieved  ...[more]

Similar Datasets

| S-EPMC4903023 | biostudies-literature
| S-EPMC6604716 | biostudies-literature
| S-EPMC2851978 | biostudies-literature
| S-EPMC8576821 | biostudies-literature
| S-EPMC3086471 | biostudies-literature
| S-EPMC2915247 | biostudies-other
| S-EPMC3588254 | biostudies-literature
| S-EPMC2962227 | biostudies-literature
| S-EPMC3163046 | biostudies-literature
| S-EPMC2749982 | biostudies-literature