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Expedient enantioselective synthesis of cermizine D.

ABSTRACT: An efficient enantioselective synthesis of cermizine D has been developed that exploits the use of a common intermediate to access over 85% of the carbon backbone. Key steps include an organocatalyzed heteroatom Michael addition, a diastereoselective alkylation with ?-iodomethyl phenyl sulfide, a conjugate addition to a vinyl sulfone species, and a sulfone coupling/desulfurization sequence to join the two major subunits.

SUBMITTER: Veerasamy N

PROVIDER: S-EPMC3319147 | biostudies-literature | 2012 Mar

REPOSITORIES: biostudies-literature

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Expedient enantioselective synthesis of cermizine D.

Veerasamy Nagarathanam N Carlson Erik C EC Carter Rich G RG

Organic letters 20120228 6

An efficient enantioselective synthesis of cermizine D has been developed that exploits the use of a common intermediate to access over 85% of the carbon backbone. Key steps include an organocatalyzed heteroatom Michael addition, a diastereoselective alkylation with α-iodomethyl phenyl sulfide, a conjugate addition to a vinyl sulfone species, and a sulfone coupling/desulfurization sequence to join the two major subunits. ...[more]

PMID: 22372610

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