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Author(s): Paek SM; Yun H; Kim NJ; Jung JW; Chang DJ; Lee S; Yoo J; Park HJ; Suh YG
Title: Concise Syntheses of (+)-Macrosphelides A and B: Studies on the Macro-Ring Closure Strategy
Source: JOURNAL OF ORGANIC CHEMISTRY 74 (2): 554-561
Date: 2009 JAN 16
Document Type: Journal : Article
DOI:
Language: English
Comment:
Address: Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea.
Sungkyunkwan Univ, Coll Pharm, Suwon 440746, South Korea. Reprint: Suh, YG, Seoul Natl Univ, Coll Pharm, Gwanak Ro 599, Seoul 151742,
South Korea. E-mail: ygsuh@snu.ac.kr
Author Keywords:
KeyWords Plus: CELL-CELL ADHESION; ORALLY BIOAVAILABLE INHIBITORS; MACROSPHELIDE-E-G;
NATURAL-PRODUCTS; ABSOLUTE STEREOCHEMISTRIES; EFFICIENT SYNTHESIS;
CLOSING METATHESIS; SEA HARE; KETONES; (+)-BREFELDIN-A
Abstract: Highly concise syntheses of (+)-macrosphelides A and B were accomplished in this study. The key feature of our synthetic route involved the direct three-carbon homologation of the readily available Weinreb amide 6 by the addition of a trans-vinylogous ester anion equivalent and facile construction of the 16-membered macrolide skeleton of macrosphelides via an intramolecular nitrile oxide-olefin cycloaddition. The syntheses of macrosphelides A and B were completed with a 30 and 20% overall yield, respectively. This paper describes the details of our syntheses.
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