TY - JOUR
T1 - Total synthesis of paniculide a from D-glucose
AU - Amano, Seiji
AU - Takemura, Noriaki
AU - Ohtsuka, Masami
AU - Ogawa, Seiichiro
AU - Chida, Noritaka
N1 - Funding Information:
We thank Professor Amos B. Smith, III (University of Pennsylvania, Philadelphia, U.S.A.) for providing us with the authentic sample of paniculide A and spectral data of his synthetic intermediates. Financial support of the Grant-in Aid for Scientific Research on Priority Area from the Ministry of Education, Science, Sports and Culture, of Japanese Government is gratefully acknowledged.
PY - 1999/3/26
Y1 - 1999/3/26
N2 - The chiral total synthesis of paniculide A (1), a highly oxygenated sesquiterpene possessing a bisabolane skeleton, starting from D-glucose is described. The two different approaches, both involved Ferrier's carbocyclization reaction to construct the cyclohexane unit in 1, were explored. The first approach, employing the carbocyclization of bicyclic substrate furnished the formal total synthesis. The second approach, designed to suppress the undesired side reactions observed in the first one, adopted the carbocyclization of a monocyclic substrate, and Claisen rearrangement for the stereoselective carbon-carbon bond formation. The successful total synthesis of I revealed the effectiveness of the combination of Ferrier's carbocyclization and Claisen rearrangement for the chiral synthesis of highly oxygenated natural products possessing cyclohexane units.
AB - The chiral total synthesis of paniculide A (1), a highly oxygenated sesquiterpene possessing a bisabolane skeleton, starting from D-glucose is described. The two different approaches, both involved Ferrier's carbocyclization reaction to construct the cyclohexane unit in 1, were explored. The first approach, employing the carbocyclization of bicyclic substrate furnished the formal total synthesis. The second approach, designed to suppress the undesired side reactions observed in the first one, adopted the carbocyclization of a monocyclic substrate, and Claisen rearrangement for the stereoselective carbon-carbon bond formation. The successful total synthesis of I revealed the effectiveness of the combination of Ferrier's carbocyclization and Claisen rearrangement for the chiral synthesis of highly oxygenated natural products possessing cyclohexane units.
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U2 - 10.1016/S0040-4020(99)00096-4
DO - 10.1016/S0040-4020(99)00096-4
M3 - Article
AN - SCOPUS:0033605880
SN - 0040-4020
VL - 55
SP - 3855
EP - 3870
JO - Tetrahedron
JF - Tetrahedron
IS - 13
ER -