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A Facile Route to Bulladecin-Type Acetogenins - Total Synthesis of Asimilobinand Correction of the Configuration of Its Tetrahydrofuran Segment (2000)

Wang, Zhi-Min ; Tian, Shi-Kai ; Shi, Min

Weinheim : Wiley-Blackwell

Liebigs Annalen 2000 (2000), S. 349-356

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ISSN: 1434-193X

Keywords: Sharpless asymmetric dihydroxylation ; Asimilobin ; Tetrahydrofuran ring ; Wittig reactions ; Annonaceous acetogenins ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: ---The most efficient method for the synthesis of the trans/threo/trans-bis(tetrahydrofuran) (THF) ring unit was established, and the first total synthesis of (-)-asimilobin and its diastereomer was then accomplished in twelve and fourteen steps, respectively, from trans-1,5,9-decatriene, by a convergent route with a Wittig reaction as the key step. By virtue of these synthetic results, the absolute configuration of the bis(THF) unit in naturally occurring asimilobin should be corrected.

Additional Material: 3 Ill.

Type of Medium: Electronic Resource

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