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Asymmetric total synthesis of epolactaene. Part 2: Introduction of the side chain and synthesis of (+)-epolactaene and its enantiomer

โœ Scribed by Shinji Marumoto; Hiroshi Kogen; Shunji Naruto

Book ID
104209439
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
748 KB
Volume
55
Category
Article
ISSN
0040-4020

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โœฆ Synopsis

A total synthesis of the novel neuritogenic agent (+)-epolactaene ((+)-1) has been achieved v/a a convergent route that utilized epoxyamide 8, C7-C11 fragment 7, and C1--C6 Wittig reagent derived from phosphonium salt 19 followed by cyclizafion to form the lactam. The absolute configuration of natural epolactaene is definitively established as (13R, 14R). Synthesis of (-)-1, the enantiomer of this natural epolactaene, is also described.

๐Ÿ“œ SIMILAR VOLUMES

Asymmetric total synthesis of epolactaen
Asymmetric total synthesis of epolactaene. Part 1: Construction of epoxy-ฮณ-lactam moiety and deduction of absolute stereochemistry
โœ Shinji Marumoto; Hiroshi Kogen; Shunji Naruto ๐Ÿ“‚ Article ๐Ÿ“… 1999 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 997 KB

Enantioselective construction of the epoxy-T-lactam moiety of epolactaenc (1) was completed in 11 steps from (R)-lactaldehyde derivatives. Key steps include: (i) the stereoselective aldol reaction between (R)lactaldehyde and malonate ester; (ii) diastereospecific lactoniTation of malonate ester deri