Total synthesis and determination of the absolute configuration of 5,6-dihydro-α-pyrone natural product synargentolide B

Prasad, Kavirayani R. ; Gutala, Phaneendra (2013) Total synthesis and determination of the absolute configuration of 5,6-dihydro-α-pyrone natural product synargentolide B The Journal of Organic Chemistry, 78 (7). pp. 3313-3322. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo400083v

Related URL: http://dx.doi.org/10.1021/jo400083v

Abstract

Enantiospecific total synthesis and determination of the absolute stereochemistry of the α-pyrone-containing natural product synargentolide B were accomplished. The absolute stereochemistry of the natural product was established by synthesizing the possible diastereomers and comparison of the data with those reported for the natural product. During the process, total synthesis of the putative structure of related natural product 6R-[1S,2R,5R,6S-(tetraacetyloxy)-3E-heptenyl]-5,6-dihydro-2H-pyran-2-one was also accomplished and confirmed by X-ray crystal structure analysis. Wittig–Horner reaction of a chiral phosphonate derived from (S)-lactic acid and ring-closing metathesis were the key reactions during the course of the total synthesis.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:105646
Deposited On:21 Dec 2017 12:02
Last Modified:21 Dec 2017 12:02

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