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Total Synthesis of Carba- d -fructofuranose via a Novel Metathesis Reaction

✍ Scribed by Seepersaud, Mohindra; Al-Abed, Yousef

Book ID: 126995440
Publisher: American Chemical Society
Year: 1999
Tongue: English
Weight: 43 KB
Volume: 1
Category: Article
ISSN: 1523-7060
DOI: 10.1021/ol990275n

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ChemInform Abstract: Total Synthesis of

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Carba-D-fructofuranose (2a) was synthesized in 3 steps from cyclopentene 3. Compound 3 was prepared in 90% yield from commercially available 2,3,5-tri-O-benzyl-D-arabinose. The C-5 hydroxylmethyl unit was incorporated into 3 via hydroformylation using Wilkinson's catalyst. Reduction and hydrogenatio

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A new total synthesis of the novel lactone natural product octalactin A is described. The key step involves the facile construction of the eight-membered lactone core via ring-closing metathesis (RCM). This oxocene was elaborated to give the powerful antitumor agent octalactin A.

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