Novel Synthesis of (−)‐(R)‐Cembrene A, Synthesis of (+)‐(R)‐Cembrenene and (+)‐(S)‐Cembrene
A novel synthesis of (−)‐(R)‐cembrene A ((−)‐3) was developed using the Sharpless epoxidation for the introduction of the chiral center. Furthermore, the synthesis of (+)‐(R)‐cembrenene ((+)‐4) showed that this cembranoid must have the (R)‐configuration and not, as previously reported, the (S)‐configuration. Selective hydrogenation of (+)‐4 afforded (+)‐(S)‐cenibrene ((+)‐5).
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