The Total Synthesis of (±)-Epi-mayol(Ⅱ)

Abstract

Abstract: The total synthesis of(±)-epi-mayol(1)using hydroxygeranial(2)and linalool (5)as starting material was described.2,6-Dimethyl-8,8-diethoxy-octa-2,6-dieneyl-p-tosylate(4)was prepared from(2),and 8-hydroxy-3,7-dimethyl-octa-2,6-dieneyl-phenylsulfone(7)was prepared from(5).Then(4)and(7)were condensed in the presence of NaNH₂ afford to the intermediate 16-hydroxy-3,7,11,15-tetramethyl-9-phenylsulfonyl-hexadeca-2,6,10,14-tetraene-al(8).8 was converted to bromide(9)and followed by ring closure in the presence of Cr(Ⅱ)to form a macrocyclic diterpene.The resulted mixture was purified by flash chromatography with high performance silicagel to obtain pure(10).Finally,the sulfonyl group of 10 was eliminated by sodium amalgam to give 1 in 8.5% overall yield.

Key words: Diterpene, Epi-mayol, 16-Dehydro-mukurol, E-1-Hydroxy-neocembrene, Condensation

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WANG Gui-Yang-Sheng, SU Jing-Yu, ZENG Long-Mei. The Total Synthesis of (±)-Epi-mayol(Ⅱ)[J]. Chem. J. Chinese Universities, 1996, 17(11): 1734.

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The Total Synthesis of (±)-Epi-mayol(Ⅱ)

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