Samarium(II) iodide-mediated reductive cyclization approach to total synthesis of the insect sex Attractant (−)-anastrephin
✍ Scribed by Kin-ichi Tadano; Yoshiaki Isshiki; Masaki Minami; Seiichiro Ogawa
- Publisher
- Elsevier Science
- Year
- 1992
- Tongue
- French
- Weight
- 280 KB
- Volume
- 33
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Abstracti Intramolecular reductive cyclization of enantiomerically pure. y,y-differentially C-substituted a&unsaturated ester 5 having a terminal aldehyde functionality, was effectively achieved using SmI2 in THF-HMF'A.
Starting with the major cyclization product 6. enantiospecific total synthesis of (-)-anastrephin 1 was completed.
Owing to their potency to create a carbon-carbon bond, reductive coupling reactions mediated by lanthanides such as Sm(I1) iodide have been extensively investigated in recent years.1
Applications of the SmI2-mediated reductive coupling reactions to substrates having two carbonyl functionalities in the molecules can provide tiveand six-membered carbocycles.
We have studied currently several approaches to enantiomerically pure carbocycles.2 Herein, we report result of the SmI2-mediated intramolecular reductive coupling reaction of a D glucose-derived substrate such as 5. 3 The major product obtained by the reductive cyclization 6 could be