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Synthetic studies on the bryostatins: synthetic routes to analogues containing the tricyclic macrolactone core.

ABSTRACT: [reaction: see text]. Synthesis of the first of a projected series of bryostatin analogues has been accomplished in 26 steps and 2.2% overall yield. In this letter, we detail two approaches to the structural core of these tricyclic macrolactone bryostatin analogues. The key features of the route include BITIP-catalyzed asymmetric allylation reactions and Mukaiyama aldol reactions, a chelation-controlled allylation, pyran annulation reactions, and macrolactonization.

SUBMITTER: Keck GE

PROVIDER: S-EPMC1480407 | biostudies-literature | 2005 May

REPOSITORIES: biostudies-literature

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Synthetic studies on the bryostatins: synthetic routes to analogues containing the tricyclic macrolactone core.

Keck Gary E GE Truong Anh P AP

Organic letters 20050501 11

[reaction: see text]. Synthesis of the first of a projected series of bryostatin analogues has been accomplished in 26 steps and 2.2% overall yield. In this letter, we detail two approaches to the structural core of these tricyclic macrolactone bryostatin analogues. The key features of the route include BITIP-catalyzed asymmetric allylation reactions and Mukaiyama aldol reactions, a chelation-controlled allylation, pyran annulation reactions, and macrolactonization. ...[more]

PMID: 15901157

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