Syntheses of (-)-TAN-2483A, (-)-massarilactone B, and the fusidilactone B ring system: Revision of the structures of and syntheses of (+/-)-Waol A (FD-211) and (+/-)-Waol B (FD-212)

Xiaolei Gao; Barry B Snider

doi:10.1021/jo0358628

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Syntheses of (-)-TAN-2483A, (-)-massarilactone B, and the fusidilactone B ring system: Revision of the structures of and syntheses of (+/-)-Waol A (FD-211) and (+/-)-Waol B (FD-212)

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Syntheses of (-)-TAN-2483A, (-)-massarilactone B, and the fusidilactone B ring system: Revision of the structures of and syntheses of (+/-)-Waol A (FD-211) and (+/-)-Waol B (FD-212)

Xiaolei Gao and Barry B Snider

Journal of Organic Chemistry, Vol.69(17), pp.5517-5527

08/01/2004

DOI: https://doi.org/10.1021/jo0358628

PMID: 15307719

Abstract

Lactones - chemical synthesis

Cyclization

Furans - chemistry

Stereoisomerism

Antineoplastic Agents - chemical synthesis

Molecular Structure

Furans - chemical synthesis

Antineoplastic Agents - chemistry

Lactones - chemistry

Chemical Reactions

Organic Chemistry

The structure of waol A has been revised from 1 to 6, the vinylogue of TAN-2483A (5). Aldol reaction of hydroxybutanolides 13b,c with 2,4-hexadienal affords 12b,c, which are subjected to iodoetherification with bis(sym-collidine)IPF6 to provide 11b(c). Treatment with Et3N in CH2Cl2 completes the three-step syntheses of TAN-2483A (5) and waol A (6). Aldol reaction of hydroxybutanolide 31 with 2,4-hexadienal affords 32, which is subjected to iodoetherification to provide 34, which in turn is treated with Bu3SnCl, NaBH3CN, and oxygen to provide diol 60. Further elaboration completes the first syntheses of massarilactone B (7) and the fusidilactone B (9) ring system.

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Title: Syntheses of (-)-TAN-2483A, (-)-massarilactone B, and the fusidilactone B ring system; Synthesis of (-)-TAN-2483A. Revision of the Structures of and Syntheses of (±)-FD-211 (Waol A) and (±)-FD-212 (Waol B)
Creators: Xiaolei Gao - Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA
Barry B Snider
Publication Details: Journal of Organic Chemistry, Vol.69(17), pp.5517-5527
Publisher: United States
Grant note: GM-50151 / NIGMS NIH HHS
Identifiers: 9923958195501921
Academic Unit: Department of Chemistry
Language: English
Resource Type: Journal article

Syntheses of (-)-TAN-2483A, (-)-massarilactone B, and the fusidilactone B ring system: Revision of the structures of and syntheses of (+/-)-Waol A (FD-211) and (+/-)-Waol B (FD-212)

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