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Synthesis 1996; 1996(6): 736-740
DOI: 10.1055/s-1996-4290
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Studies on Macrocyclic Diterpenoids (XVII): Total Synthesis of (-)-Cembrene-A and (+)-3,4-Epoxycembrene-A by Titanium-Induced Carbonyl Coupling Reactions

Xiangjun Yue, Yulin Li*
  • *State Key Laboratory of Applied Organic Chemistry and Institute of Organic Chemistry, Lanzhou University, Lanzhou 730000, People’s Republic of China, Fax +86(931)8881996
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Publikationsdatum:
31. Dezember 2000 (online)

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Efficient total synthesis of (R)-cembrene-A (1) and (+)-3,4-epoxycembrene-A (2), two marine cembranoids, starting from (E)-geranylacetone (6) and (R)-limonene (7) are described. The key steps are the synthesis of olefin 12 from phosphonate 4 and optically active ketone 5 by the modified Wittig olefination, and the titanium-induced intramolecular coupling of oxo aldehyde 3 to afford cembrene-A (1). The pinacol coupling of 3 yielded the diol 13 which was converted into 3,4-epoxycembrene-A (2).

Asymmetric syntheses of two manine cembranoids (R)-cembrene-A and (+)-3,4-epoxycembrene-A from (E)-geranylacetone and (R)-limonene are described.