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Issue 40, 2020
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Total synthesis of dimeric Securinega alkaloids (−)-flueggenines D and I

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Abstract

We describe the total synthesis of (−)-flueggenines D and I. This features the first total synthesis of dimeric Securinega alkaloids with a C(α)–C(δ′) connectivity between two monomeric units. The key dimerization was enabled by a sequence that involves Stille reaction and conjugate reduction. The high chemofidelity of the Stille reaction enabled us to assemble two structurally complex fragments that could not be connected by other methods. Stereochemical flexibility and controllability at the δ′-junction of the dimeric intermediate render our synthetic strategy broadly applicable to the synthesis of other high-order Securinega alkaloids.

Graphical abstract: Total synthesis of dimeric Securinega alkaloids (−)-flueggenines D and I

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Supplementary files

Article information


Submitted
01 Jun 2020
Accepted
06 Sep 2020
First published
07 Sep 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, 10934-10938
Article type
Edge Article

Total synthesis of dimeric Securinega alkaloids (−)-flueggenines D and I

S. Jeon, J. Lee, S. Park and S. Han, Chem. Sci., 2020, 11, 10934
DOI: 10.1039/D0SC03057K

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