Synthesis of (−)-TAN-2483A. Revision of the Structures and Syntheses of (±)-FD-211 (Waol A) and (±)-FD-212 (Waol B)

Xiaolei Gao; Masakazu Nakadai; Barry B Snider

doi:10.1021/ol0273405

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Synthesis of (−)-TAN-2483A. Revision of the Structures and Syntheses of (±)-FD-211 (Waol A) and (±)-FD-212 (Waol B)

Journal article

Peer reviewed

Synthesis of (−)-TAN-2483A. Revision of the Structures and Syntheses of (±)-FD-211 (Waol A) and (±)-FD-212 (Waol B)

Xiaolei Gao, Masakazu Nakadai and Barry B Snider

Organic letters, Vol.5(4), pp.451-454

02/01/2003

DOI: https://doi.org/10.1021/ol0273405

PMID: 12583741

Abstract

Absorption

Mixtures

Chemical structure

Molecular structure

Aldol reactions

The structure of waol A has been revised from 1 to 6, the vinylogue of TAN-2483 A (5). Aldol reaction of 10b(c) with 2,4-hexadienal (11) affords 9b(c), which is subjected to iodoetherification with bis(sym-collidine)IPF6 to provide 8b(c). Treatment with Et3N in CH2Cl2 completes three-step syntheses of TAN-2483A (5) and waol A (6).

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Title: Synthesis of (−)-TAN-2483A. Revision of the Structures and Syntheses of (±)-FD-211 (Waol A) and (±)-FD-212 (Waol B)
Creators: Xiaolei Gao - Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110
Masakazu Nakadai - Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110
Barry B Snider - Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110
Publication Details: Organic letters, Vol.5(4), pp.451-454
Identifiers: 9924012820701921
Academic Unit: Department of Chemistry
Language: English
Resource Type: Journal article

Synthesis of (−)-TAN-2483A. Revision of the Structures and Syntheses of (±)-FD-211 (Waol A) and (±)-FD-212 (Waol B)

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