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Synthesis of a New (1R)-(-)-myrtenal-derived Dioxadithiadodecacycle and Its Use as an Efficient Chiral Auxiliary

Synthesis of a New (1R)-(-)-myrtenal-derived Dioxadithiadodecacycle and Its Use as an Efficient Chiral Auxiliary

M Elena Vargas-Díaz, Pedro Joseph-Nathan, Joaquín Tamariz, L Gerardo Zepeda

Org Lett. 2007 Jan 4;9(1):13-6.

PMID: 17192073

Abstract:

[reaction: see text] The new macrocycle 9 (>70% yield from hydroxythiol 10) was treated with several nucleophilic reagents (RMgX, RLi, and LiAlH4) affording carbinols 12a-j (80-96% yield, >99:1 dr). Oxidative hydrolysis of 12a,c,e, followed by LiAlH4 reduction of the resulting mixture, gave 16a,c,e in >95% ee,16c being a key precursor for the preparation of fungicide 17. The absolute configuration of 9 and 12j (Nu = H) was established by single-crystal X-ray diffraction analyses and chemical correlation.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP18486696	(1R)-(−)-Myrtenal		18486-69-6	Price

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