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Synfacts 2022; 18(07): 0809
DOI: 10.1055/s-0041-1737644
Chemistry in Medicine and Biology

The First Total Synthesis of Bryostatin 7

Contributor(s):
Dirk Trauner
,
Matthew DiCairano
Kageyama M, Tamura T, Nantz MH, Roberts JC, Somfai P, Whritenour DC, Masamune S. * Massachusetts Institute of Technology, Cambridge, USA
Synthesis of Bryostatin 7.

J. Am. Chem. Soc. 1990;
112: 7407-7408
DOI: 10.1021/ja00176a058.
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Key words

bryostatin 7 - Julia–Lythgoe olefination - aldol reaction

Significance

The bryostatins are a family of 21 marine natural products boasting a wide range of biological activities. They have been explored as anticancer­ agents, treatments for Alzheimer’s disease, and as antivirals against HIV. Of this family, the first to succumb to total synthesis was bryostatin 7 in a heroic synthesis by the Masamune group requiring a total of 79 steps with a 41 step longest linear sequence.


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Comment

Retrosynthetically, bryostatin 7 was broken into three fragments (A, B, and D). A and B were used for a matched aldol reaction followed by Hg-mediated cyclization. Further manipulations yielded C. Fragment D (prepared in 22 steps) underwent a Julia–Lythgoe olefination with C to complete the unification of all fragments. A DCC-mediated macrocyclization was used to close the lactone.


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Publication History

Article published online:
15 June 2022

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