Total Synthesis of (±)-Nimbonone and (±)-12-Ethyl-13-methoxy-8,11,13-podocarpatriene

Chem. J. Chinese Universities ›› 2003, Vol. 24 ›› Issue (6): 1019.

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Total Synthesis of (±)-Nimbonone and (±)-12-Ethyl-13-methoxy-8,11,13-podocarpatriene

ZHANG Cheng-Lu^1,2, BIE Ping-Yan¹, PENG Xuan-Jia¹, PAN Xin-Fu¹

1. Department of Chemistry, National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China;
2. Department of Chemistry, Liaoning Normal University, Dalian 116029, China

Received:2002-05-28 Online:2003-06-24 Published:2003-06-24

Abstract

Abstract: BYUsing α-cyclocitral(1) as the A ring synthon, and triphenyl phosphonium chloride(2) as the C ring synthon, the keYINtermediate 5 was obtained after the condensation and intracyclization reactions. In order to introduce the ethyl substituent, Fiedel-Crafts acetylation had been first employed to synthesize compound 6, and then the carbonyl group in compound 6 was protected with 1,2-ethanedithiol to afford compound 7. Compound 7 was oxidized to afford compound 8. Desulfurization of compounds 7 and 8 with Raney Ni gave the desired products (±)-nimbonone (9) and (±)-12-ethyl-13-methoxy-8,11,13-podocarpatriene (10) respectively.

Key words: Total synthesis, Tricyclic diterpenes, (±)-Nimbonone

CLC Number:

O629

TrendMD:

ZHANG Cheng-Lu, BIE Ping-Yan, PENG Xuan-Jia, PAN Xin-Fu. Total Synthesis of (±)-Nimbonone and (±)-12-Ethyl-13-methoxy-8,11,13-podocarpatriene[J]. Chem. J. Chinese Universities, 2003, 24(6): 1019.

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Total Synthesis of (±)-Nimbonone and (±)-12-Ethyl-13-methoxy-8,11,13-podocarpatriene

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