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Literature DB >> 12375911

Synthesis of the C10-C22 bis-spiroacetal domain of spirolides B and D via iterative oxidative radical cyclization.

Abstract

[reaction: see text] A synthetic approach to the novel bis-spiroacetal moiety of spirolides B and D is reported. The strategy hinges upon successive formation of the spirocenters at C15 and C18 by radical oxidative cyclization, followed by base-induced rearrangement of a C19-20 alpha-epoxide to introduce the C19 hydroxyl group.

Entities: Chemical Gene

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Year: 2002 PMID： 12375911 DOI： 10.1021/ol026605c

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

6 in total

Review 1. Synthesis and biology of cyclic imine toxins, an emerging class of potent, globally distributed marine toxins.

Authors: Craig E Stivala; Evelyne Benoit; Rómulo Aráoz; Denis Servent; Alexei Novikov; Jordi Molgó; Armen Zakarian
Journal: Nat Prod Rep Date: 2015-03 Impact factor: 13.423

2. Studies toward the synthesis of spirolide C: exploration into the formation of the 23-membered all-carbon macrocyclic framework.

Authors: Craig E Stivala; Zhenhua Gu; Lindsay L Smith; Armen Zakarian
Journal: Org Lett Date: 2012-01-19 Impact factor: 6.005

Synthesis of the C10-C22 bis-spiroacetal domain of spirolides B and D via iterative oxidative radical cyclization.

Review 1. Synthesis and biology of cyclic imine toxins, an emerging class of potent, globally distributed marine toxins.

2. Studies toward the synthesis of spirolide C: exploration into the formation of the 23-membered all-carbon macrocyclic framework.

3. Total synthesis of the spirocyclic imine marine toxin (-)-gymnodimine and an unnatural C4-epimer.

4. Radical oxidative cyclization of spiroacetals to bis-spiroacetals: an overview.

5. Studies toward the synthesis of spirolides: assembly of the elaborated E-ring fragment.

6. A reductive cyclization approach to attenol A.