Synthesis of bryostatins. 1. Construction of the C(1)-C(16) fragment

Mary A. Blanchette, Michael S. Malamas, Michael H. Nantz, John C. Roberts, Peter Somfai, David C. Whritenour, Satoru Masamune, Masanori Kageyama, Tadashi Tamura

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104 Scopus citations

Abstract

The synthesis of fragment AB [C(1)-C(16)] of bryostatin 1 is described. Two aldol coupling reactions involving (i) chiral fragment A [C(1)-C(10)] with achiral B [C(11)-C(16)] and (ii) chiral fragment A1 [C(7)-C(10)] with achiral A2 [C(6)-C(1)] constitute crucial steps in which an external chiral boron reagent is used to control stereoselectivity in the creation of a new stereogenic center. This type of double asymmetric synthesis, although rarely precedented, provides a powerful means of stereocontrol over the fragment assembly.

Original languageEnglish (US)
Pages (from-to)2817-2825
Number of pages9
JournalJournal of Organic Chemistry
Volume54
Issue number12
StatePublished - 1989
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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    Blanchette, M. A., Malamas, M. S., Nantz, M. H., Roberts, J. C., Somfai, P., Whritenour, D. C., Masamune, S., Kageyama, M., & Tamura, T. (1989). Synthesis of bryostatins. 1. Construction of the C(1)-C(16) fragment. Journal of Organic Chemistry, 54(12), 2817-2825.