A modular strategy for the synthesis of marine originated meroterpenoid-type natural products

• Published in: Organic & biomolecular chemistry Vol. 19; no. 43; pp. 9439 - 9447
• Main Authors: Wang, Hong-Shuang, Nan, Xiang, Li, Hui-Jing, Cao, Zhong-Yan, Wu, Yan-Chao
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 10.11.2021; Royal Society of Chemistry
• Subjects: Chemistry; Chemistry, Organic; Natural products; Palladium; Physical Sciences; Science & Technology; DIVERGENT SYNTHESIS; METABOLITES; REAGENTS; ANALOGS; PUUPEHENONE; N-TOSYLHYDRAZONES
• ISSN: 1477-0520; 1477-0539; 1477-0539
• DOI: 10.1039/d1ob01598b

A modular strategy for meroterpenoid-type marine natural products has been developed from commercially available (+)-sclareolide using a palladium-catalyzed tandem carbene migratory insertion as one of the key steps. Its applicability is showcased by the formal synthesis of (−)-pelorol and 9- epi -pelorol and the concise total synthesis of (+)-yahazunone and (+)-yahazunol. It is worth noting that the formal synthesis of (−)-pelorol and 9- epi -pelorol was achieved by controlling the reaction sequence of hydrogenation and cyclization. Chemoselective formal synthesis of (−)-pelorol and 9- epi -pelorol was achieved by controlling the reaction sequence of hydrogenation and cyclization. Synthesis of (+)-yahazunone and (+)-yahazunol was also accomplished using palladium-catalyzed tandem carbene migratory insertion.