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Issue 27, 2020
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Total synthesis of crotophorbolone

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Abstract

As a natural diterpenoid, crotophorbolone possesses a challenging trans,trans-5/7/6 framework decorated with six contiguous stereogenic centers and is structurally and biogenetically related to tigliane-type diterpenoids with intriguing bioactivities such as phorbol and prostratin. Based on the convergent strategy, we completed an eighteen-step total synthesis of crotophorbolone starting from (−)-carvone and (+)-dimethyl-2,3-O-isopropylidene-L-tartrate. The key elements of the synthesis involve expedient installation of the six-membered ring and the five-membered ring with multiple functional groups at an early stage, cyclization of the seven-membered ring through alkenylation of the ketone between the five-membered ring and the six-membered ring, functional group-sensitive ring-closing metathesis and final selective introduction of hydroxyls at C20 and C4.

Graphical abstract: Total synthesis of crotophorbolone

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Supplementary files

Article information


Submitted
18 May 2020
Accepted
17 Jun 2020
First published
19 Jun 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 7177-7181
Article type
Edge Article

Total synthesis of crotophorbolone

T. Yu, Y. Sun, C. Tu, T. Chen, S. Fu and B. Liu, Chem. Sci., 2020, 11, 7177
DOI: 10.1039/D0SC02829K

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