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黄培强 , Pei-Qiang Huang, * Hong-Qiao Lan, Xiao Zheng, and Yuan-Ping Ruan
J. Org. Chem., Vol. 69, No. 11, 2004,-0001,():
-1年11月30日
(2S,3S,7S)-3,7-Dimethylpentadecan-2-yl acetate (2) and its propionate analogue (3) are the main sex pheromones of all Neodiprion species and Diprion similes, respectively. Starting from (S)-malic acid and employing a highly chemo-, regio-, and stereoselective tandem ester reduction-epoxide formation-reductive epoxide-opening reaction protocol, an efficient total synthesis of (2S,3S,7S)-2 and -3 is reported herein.
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黄培强 , Bi-Yan He, Tian-Jun Wu, Xian-Yong Yu and Pei-Qiang Huang*
Tetrahedron: Asymmentry 14(2003)2101-2108,-0001,():
-1年11月30日
A flexible non-amino acid-based formal asymmetric synthesis of naturally occurring antimicrobial (2R,3S)-2-aminotetradeca-5,7-dien-3-ol is reported. The method features a flexible and highly regioselective Grignard addition to (S)-malimide followed by a trans-diastereoselective reductive deoxygenation. The scope and limitations of the highly regio and diastereoselective reductive alkylation of malimides were defined. A remarkable protecting group effect on the regio and diastereoselective reductive alkylation of malimides was observed.
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黄培强 , Pei-Qiang Huang, * Tian-Jun Wu, and Yuan-Ping Ruan
Lett., Vol. 5, No. 23, 2003,-0001,():
-1年11月30日
A flexible asymmetric approach to 5-alkyl tetramic acid derivatives is described, which is based on the use of 9 as the first synthetic equivalent to chiral nonracemic tetramic acid 5-carbanionic synthon 9b. The existence of the carbanion intermediate 9b was proven by trapping with trimethylchlorosilane. Application of the present method to the synthesis of antifungal alkaloid (+)-preussin, as well as protected (3S,4S)-AHPPA 6, is also described.
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黄培强 , Pei-Qiang Huang, * Liang-Xian Liu, Bang-Guo Wei, and Yuan-Ping Ruan
Org. Lett., Vol. 5, No. 11, 2003,-0001,():
-1年11月30日
Selective and potent neurokinin substance P receptor antagonists (+)-L-733, 060 (1) and (+)-CP-99, 994 (2) have been synthesized starting from a new (3S)-piperidinol synthon derived from L-glutamic acid. The methods featured a C-2 regioselective reduction of glutarimide (9), Lewis acid-promoted Si to C-2 phenyl group migration of 10, and stereoselective reduction of acetylated oxime 19 as the key steps.
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黄培强 , Liang-Xian Liu, Yuan-Ping Ruan, Zheng-Qing Guo, and Pei-Qiang Huang*
J. Org. Chem. 2004, 69, 6001-6009,-0001,():
-1年11月30日
A general approach to (5S,6R)-6-alkyl-5-benzyloxy-2-piperidinones based on the regioand diastereoselective reductive alkylation of (S)-3-benzyloxyglutarimide 7 is described. This method opens an entrance to chiral nonracemic substituted 3-piperidinols. The versatility of the method is illustrated by the asymmetric syntheses of neurokinin substance P receptor antagonist L-733,061 (ent-1), (-)-deoxocassine (4), and an inhibitor of HIV proteases (5a).
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