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Antineoplastic agents. 571. Total synthesis of bacillistatin 2.

ABSTRACT: The first total synthesis of bacillistain 2 (2) has been achieved in 24 steps and 22.9% overall yield, providing a quite efficient route with maximal convergence. Notable features of this approach include two successful applications of the Mitsunobu reaction during respective assemblies of key intermediates 22 and 27, successful employment of 2-methyl-6-nitrobenzoic anhydride (MNBA) in the formation by lactonization of a macrocyclic (36-membered) ring, and very flexible access to structural modifications of the bacillistatin-type cyclodepsipeptides.

SUBMITTER: Pettit GR

PROVIDER: S-EPMC2837129 | biostudies-literature | 2009 Mar

REPOSITORIES: biostudies-literature

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Antineoplastic agents. 571. Total synthesis of bacillistatin 2.

Pettit George R GR Hu Shougang S Knight John C JC Chapuis Jean-Charles JC

Journal of natural products 20090301 3

The first total synthesis of bacillistain 2 (2) has been achieved in 24 steps and 22.9% overall yield, providing a quite efficient route with maximal convergence. Notable features of this approach include two successful applications of the Mitsunobu reaction during respective assemblies of key intermediates 22 and 27, successful employment of 2-methyl-6-nitrobenzoic anhydride (MNBA) in the formation by lactonization of a macrocyclic (36-membered) ring, and very flexible access to structural modi ...[more]

PMID: 19216517

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