期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 41, 页码 12498-12502出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201705654
关键词
biosynthesis; density-functional calculations; natural products; terpenoids; total synthesis
资金
- NSF (CAREER Award) [155454]
- NSF [CHE-1565933, CHE-030089]
- Swiss National Science Foundation (SNSF) [P2BEP2_162076]
- NIH Shared Instrument Grant [S10-RR027172]
- High Performance Computing facilities
- Direct For Mathematical & Physical Scien [1554544] Funding Source: National Science Foundation
- Division Of Chemistry [1554544] Funding Source: National Science Foundation
- Swiss National Science Foundation (SNF) [P2BEP2_162076] Funding Source: Swiss National Science Foundation (SNF)
Meroterpenes derived from dimethylorsellinic acid (DMOA) and farnesyl pyrophosphate have attracted much biosynthetic attention, yet only recently have synthetic solutions to any family members appeared. A key point of divergence in DMOA-derived meroterpene biosynthesis is the protoaustinoidA carbocation, which can be diverted to either the berkeleyone, andrastin, or terretonin structural classes by cyclase-controlled rearrangement pathways. Shown herein is that the protoaustinoid bicyclo[3.3.1]nonane nucleus can be reverted to either andrastin or terretonin ring systems under abiotic reaction conditions. The first total syntheses of members of these natural product families are reported as their racemates.
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