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Volumn 37, Issue 19, 1998, Pages 2675-2678

A novel aldol condensation with 2-methyl-4-pentenal and its application to an improved total synthesis of epothilone B

Author keywords

Aldol reactions; Epothilones; Natural products; Suzuki coupling; Total synthesis

Indexed keywords


EID: 0032538477     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981016)37:19<2675::AID-ANIE2675>3.0.CO;2-O     Document Type: Article
Times cited : (73)

References (53)
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    • note
    • [16a] assuming that this isomer arises from facial selectivity in the aldol reaction and not as a consequence of the E configuration of the enolate group of 10. Similarly, the stereochemistry assigned as the syn,syn products 14 was not proven in each case. Those assignments also rely to varying extents on the examples given in ref. [16a].
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    • The Noyori reduction of various diketo esters was very dependent on the amount of acid in the reaction mixture. Without the presence of stoichiometric acid, the rate of reduction and the selectivity dropped in the reduction. At higher pressures, the chemoselectivity of the reduction was poor resulting in reduction of both of the alkene groups. Furthermore, the carbonyl group at C5 was never reduced under these conditions, but was absolutely necessary for the reduction of the carbonyl group at C3. When an alcohol functionality was at C5, no reduction was seen. A. Balog, unpublished results.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.