Beilstein J. Org. Chem.2023,19, 428–433, doi:10.3762/bjoc.19.32
, France 10.3762/bjoc.19.32 Abstract Latrunculins are marine toxins used in cell biology to block actin polymerization. The development of new synthetic strategies and methods for their synthesis is thus important in order to improve, modulate or control this biological value. The total syntheses found in
the natural products.
Keywords: allylation; aldol reaction; latrunculins; stereocontrol; total synthesis; Introduction
Latrunculins constitute a class of marine polyketide natural products isolated from Sponges like Negombata (= Latrunculia) magnifica [1][2]. They are characterized by the presence
of an unsaturated fourteen- or sixteen-membered macrolactone decorated by an ʟ-cysteine-derived 2-oxo-1,3-thiazolidin-4-yl substitutent, and the presence of five stereogenic centers forming a 1,2,4,6,9-stereopentade (Figure 1). In latrunculins A (1) and B (2) three of them are embedded in a lactol
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Graphical Abstract
Figure 1:
Structure of latrunculins (the red dots show the natural product stereopentade).