Substitution on the A-Ring Confers to Bryopyran Analogues the Unique Biological Activity Characteristic of Bryostatins and Distinct From That of the Phorbol Esters

Keck, Gary E.; Poudel, Yam B.; Welch, Dennie S.; Kraft, Matthew B.; Truong, Anh P.; Stephens, Jeffrey C.; Kedei, Noemi; Lewin, Nancy E.; Blumberg, Peter M.

doi:10.1021/ol8027253.s001

ol8027253_si_001.pdf (1.88 MB)

Substitution on the A-Ring Confers to Bryopyran Analogues the Unique Biological Activity Characteristic of Bryostatins and Distinct From That of the Phorbol Esters

journal contribution

posted on 2009-02-05, 00:00 authored by Gary E. Keck, Yam B. Poudel, Dennie S. Welch, Matthew B. Kraft, Anh P. Truong, Jeffrey C. Stephens, Noemi Kedei, Nancy E. Lewin, Peter M. Blumberg

A close structural analogue of bryostatin 1, which differs from bryostatin 1 only by the absence of the C₃₀ carbomethoxy group (on the C₁₃ enoate of the B-ring), has been prepared by total synthesis. Biological assays reveal a crucial role for substitution in the bryostatin 1 A-ring in conferring those responses which are characteristic of bryostatin 1 and distinct from those observed with PMA.