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. 2011 May 6;13(9):2384-7.
doi: 10.1021/ol200627d. Epub 2011 Apr 8.

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

Daniel P Canterbury  1 , Glenn C Micalizio
Affiliations

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

Daniel P Canterbury et al. Org Lett. .

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.

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Figures

Figure 1
Figure 1
Introduction to the pectenotoxins.
Scheme 1
Scheme 1
Synthetic strategy for a model CDEF tetracycle.
Scheme 2
Scheme 2
Preparation of linalool-derived coupling partners.
Scheme 3
Scheme 3
Convergent coupling en route to a DEF-tricycle.
Scheme 4
Scheme 4
Synthesis of C-ring fragment precursor.
Scheme 5
Scheme 5
Generation of a CDEF tetracycle.
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