Shimizu Emily A, Rychnovsky Scott D
Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, Irvine, California 92697, United States.
Org Lett. 2025 Jun 13;27(23):6170-6173. doi: 10.1021/acs.orglett.5c01802. Epub 2025 Jun 2.
Reported herein is the first total synthesis of the acorane-type terpenoid rhodocorane L, isolated from the fungus . This unique tricyclic scaffold containing a spiro[4.5] bicycle has antifungal activity. Key steps include diastereoselective cuprate addition, gold-catalyzed dearomative spirocyclization, and intramolecular aldol. This is the first time that a catalyst-controlled asymmetric dearomative spirocyclization has been utilized in a total synthesis. Rhodocorane L was synthesized in 17 steps, as the longest linear sequence.
本文报道了从真菌中分离出的菖蒲烷型萜类化合物红菖蒲烷L的首次全合成。这种独特的含有螺[4.5]双环的三环骨架具有抗真菌活性。关键步骤包括非对映选择性铜酸盐加成、金催化的去芳构化螺环化反应和分子内羟醛缩合反应。这是首次在全合成中使用催化剂控制的不对称去芳构化螺环化反应。红菖蒲烷L以最长线性序列经17步合成得到。
