Journal
SYNLETT
Volume 27, Issue 9, Pages 1428-1432Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0035-1561576
Keywords
anastrephin; quaternary carbon; asymmetric synthesis; allylic substitution; copper reagent; picolinate
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Funding
- Ministry of Education, Culture, Sports, Science, and Technology, Japan [26410111]
- Grants-in-Aid for Scientific Research [26410111] Funding Source: KAKEN
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Lactone-moiety-attached 2-cyclohexylideneethyl picolinate was prepared through the OH-directed epoxidation (98% ds) of (R)-3-methylcyclohex-2-en-1-ol (99% ee), Horner-Wadsworth-Emmons olefination, conversion to the allylic moiety, and epoxide ring opening with Et(2)AlCH(2)CO(2)t-Bu. The allylic substitution of the picolinate with Me2CuMgBrMgBr2 furnished a quaternary carbon center with 92% ds. Finally, the lactonization of the product, the tert-butyl ester of the seco acid, under acidic conditions, afforded (-)-anastrephin.
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