✍ Scribed by Tadahiro Kato; Masahiro Hoshikawa
No coin nor oath required. For personal study only.
The first synthesis of trinervita‐1(15),8(19)‐dien‐2__β__,3__α__‐diol (2a) and its 2__α__‐isomer 2b, which have been isolated from termite soldiers, where they are used as defense chemicals, is documented starting from geranylgeranioic acid in 33 steps. The route for construction of the key intermediate of the trinervitane skeleton 8 has been developed previously (Scheme 1). Noteworthy features include the efficient construction of the trinervitane framework from the corresponding bicyclic 7(16)‐secotrinervitane skeleton and Me~3~SiCl (TMSCl)‐induced ring‐opening of tetrasubstituted epoxide to give the corresponding allyl alcohols (Scheme 7). The synthetic route developed in the present study seems applicable to the syntheses of other trinervitane‐type natural products.
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