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A New Total Synthesis of dl-Pumiliotoxin-C via an Indanone

✍ Scribed by Wolfgang Oppolzer; Charles Fehr; Jochen Warneke

Publisher: John Wiley and Sons
Year: 1977
Tongue: German
Weight: 669 KB
Volume: 60
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19770600108

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✦ Synopsis

Abstract

dl‐Pumiliotoxin‐C (4) was synthesized in a practical manner from trans‐4‐hexenal (9). The key step 14 → 15 (Scheme 3) involves an intramolecular Diels‐Alder reaction giving mainly the cis‐fused indanols 15a, which were converted to the cis‐fused ketone 16. After Beckmann‐rearrangement of 16 the octahydroquinolinone 7 was transformed to the lactim‐ether 23. (Scheme 7). Reaction of 23 with propylmagnesium bromide followed by hydrogenation furnished dl‐4 in a highly stereoselective fashion.

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