TY - JOUR
T1 - Synthesis of a new (1R)-(-)-myrtenal-derived dioxadithiadodecacycle and its use as an efficient chiral auxiliary
AU - Vargas-Díaz, M. Elena
AU - Joseph-Nathan, Pedro
AU - Tamariz, Joaquín
AU - Zepeda, L. Gerardo
PY - 2007/1/4
Y1 - 2007/1/4
N2 - (Chemical Equation Presented) 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.
AB - (Chemical Equation Presented) 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.
UR - http://www.scopus.com/inward/record.url?scp=33846426442&partnerID=8YFLogxK
U2 - 10.1021/ol062319f
DO - 10.1021/ol062319f
M3 - Artículo
SN - 1523-7060
VL - 9
SP - 13
EP - 16
JO - Organic Letters
JF - Organic Letters
IS - 1
ER -