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Asymmetric synthesis of a tetracyclic model for the aziridinomitosenes

✍ Scribed by Joseph P Michael; Charles B de Koning; Riaan L Petersen; Trevor V Stanbury

Book ID
104231646
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
72 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

The conversion of (-)-2,3-O-isopropylidene-D-erythronolactone (9) into the N-phosphorylated aziridine 20, a model for the fundamental structure of aziridinomitosenes, has been accomplished in 11 steps by way of the vinylogous urethane 13. Key steps include the preparation of 13 by a Reformatsky reaction on a thiolactam precursor, Heck cyclisation of 13 to form the indole ring, and aziridine synthesis via a cyclic sulfite.

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