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Total Synthesis of (-)-Secu'amamine A Exploiting Type II Anion Relay Chemistry.

ABSTRACT: A total synthesis of (-)-secu'amamine A has been achieved exploiting Type II Anion Relay Chemistry (ARC) to provide the full linear carbon and nitrogen skeleton in a single flask with the requisite stereochemistry and functionality. A mechanistic rationale is also proposed to account for the stereochemical outcome of the key aldol reaction leading to the advanced aza tricyclic core.

SUBMITTER: Han H

PROVIDER: S-EPMC4633699 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Total Synthesis of (-)-Mandelalide A Exploiting Anion Relay Chemistry (ARC): Identification of a Type II ARC/CuCN Cross-Coupling Protocol.

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Type II Anion Relay Chemistry: Exploiting Bifunctional Weinreb Amide Linchpins for the One-Pot Synthesis of Differentiated 1,3-Diketones, Pyrans, and Spiroketals.

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Project description:Construction of the C(1)-C(25) southern fragments of both spirastrellolide A and B are described. Highlights of the syntheses include effective use of the three component anion relay chemistry (ARC) tactic recently introduced by our laboratory, a stereoselective spirocyclization via concomitant Ferrier reaction to elaborate the BC spiroketal and use of two dithiane unions to install the A ring as well as C(22)-C(25) fragment. The synthesis proceeded with longest linear sequences of 33 and 32 steps respectively for spirastrellolide A and spirastrellolide B.

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Benzyl and phenylthiomethyl silanes: a new class of bifunctional linchpins for type II anion relay chemistry (ARC).

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