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A convergent route to the CDEF-tetracycle of pectenotoxin-2.

ABSTRACT: A convergent synthesis of the CDEF-tetracyclic region of pectenotoxin-2 (PTX-2) is described. The synthetic pathway derives from a head-to-tail union of 2 equiv of linalool to establish a stereodefined DEF-tricyclic aldehyde. Subsequent coupling with a "northern" fragment enolate, followed by a tandem Sharpless epoxidation/cyclization, delivers the C10-C26 polycyclic region of the natural product.

SUBMITTER: Canterbury DP

PROVIDER: S-EPMC3156112 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature

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A convergent route to the CDEF-tetracycle of pectenotoxin-2.

Canterbury Daniel P DP Micalizio Glenn C GC

Organic letters 20110408 9

A convergent synthesis of the CDEF-tetracyclic region of pectenotoxin-2 (PTX-2) is described. The synthetic pathway derives from a head-to-tail union of 2 equiv of linalool to establish a stereodefined DEF-tricyclic aldehyde. Subsequent coupling with a "northern" fragment enolate, followed by a tandem Sharpless epoxidation/cyclization, delivers the C10-C26 polycyclic region of the natural product. ...[more]

PMID: 21476517

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