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Stereoselective construction of all-anti polypropionate modules: synthesis of the C5-C10 fragment of streptovaricin U.

ABSTRACT: A concise nonaldol approach for the stereoselective construction of all-anti polypropionate fragments was developed. The iterative epoxide-based methodology consists of the syn-selective epoxidation of cis homoallylic alcohols with use of the VO(acac)(2)-catalyzed conditions followed by epoxide cleavage with a propynyl aluminum reagent as key steps. The methodology was applied to the synthesis of the all-anti C6-C10 fragment of streptovaricin U.

SUBMITTER: Torres W

PROVIDER: S-EPMC2677810 | biostudies-literature | 2009 Mar

REPOSITORIES: biostudies-literature

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Stereoselective construction of all-anti polypropionate modules: synthesis of the C5-C10 fragment of streptovaricin U.

Torres Wildeliz W Rodríguez Raúl R RR Prieto José A JA

The Journal of organic chemistry 20090301 6

A concise nonaldol approach for the stereoselective construction of all-anti polypropionate fragments was developed. The iterative epoxide-based methodology consists of the syn-selective epoxidation of cis homoallylic alcohols with use of the VO(acac)(2)-catalyzed conditions followed by epoxide cleavage with a propynyl aluminum reagent as key steps. The methodology was applied to the synthesis of the all-anti C6-C10 fragment of streptovaricin U. ...[more]

PMID: 19236033

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