Regiocontrolled conversion of α,β-unsaturated ketones to olefins via allylsilanes: synthesis of d1-9(0)-methano-Δ6(9α)-PGI1
✍ Scribed by Masakatsu Shibasaki; Hidemi Fukasawa; Shiro Ikegami
- Book ID
- 104219993
- Publisher
- Elsevier Science
- Year
- 1983
- Tongue
- French
- Weight
- 204 KB
- Volume
- 24
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A synthesis of dl-9(O)-methano-A 6(9a)_pGI 1 (1_), a more potent prostacyclin analog than carbacyclin, has been accomplished utilizing regiocontrolled transformation of the enone to the olefin via the allylsilane as a key step.
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A key intermediate for the synthesis of isocarbacyclin, a promising therapeutic agent for cardiovascular and circulatory disorders, has been synthesized from (&J-(+)-methyl 2-oxo-l-cyclopentaneacetate by employing rhodium(II)-catalyzed intramolecular C-H insertion reaction of a-diazo B-keto ester as
## (O)-methano-A 6(9a)_pGI has been synthesized by utilizing the regiocontrolled cleavage of the B-propio&one tiith the dialkylaluminum acetylide.