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The Total Synthesis of Rhabdastrellic Acid A

preprint
submitted on 18.12.2018 and posted on 19.12.2018 by Yaroslav Boyko, Christopher Huck, David Sarlah
The first total synthesis of rhabdastrellic acid A, a highly cytotoxic isomalabaricane triterpenoid, has been accomplished in a linear sequence of 14 steps from commercial geranylacetone. The prominently strained trans-syn-trans-perhydrobenz[e]indene core characteristic of the isomalabaricanes is efficiently accessed in a selective manner for the first time through a rapid, complexity-generating sequence incorporating a reductive radical polyene cyclization, an unprecedented oxidative Rautenstrauch cycloisomerization, and umpolung 𝛼-substitution of a p-toluenesulfonylhydrazone with in situ reductive transposition. A late-stage cross-coupling in concert with a modular approach to polyunsaturated side chains renders this a general strategy for the synthesis of numerous family members of these synthetically challenging and hitherto inaccessible marine triterpenoids.

History

Email Address of Submitting Author

sarlah@illinois.edu

Institution

University of Illinois

Country

United States

ORCID For Submitting Author

0000-0002-8736-8953

Declaration of Conflict of Interest

We declare no competing financial interests.

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