The catecholic ketal core substructure of trichotomone, a dimeric abietane-type diterpenoid, was constructed. Key elements of the synthesis include an Ullmann condensation between a phenol and phenyl bromide, and the final 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated oxidative dearomatization/ketalization reaction.
The back cover picture shows Genkwadane A was isolated from the flower buds of Daphne genkwa which shows bioactivity against HeLa, HepG2, HT‐1080, MCF‐7, A549, U‐937, K562 and HL60 cell lines. It is the first time that a daphnane diterpenoid bearing a 1,10‐double bond was isolated. In this paper, B. Liu and co‐workers report asymmetric synthesis of the ring A substructure of genkwadane A in 10 steps from D‐tartrate derivative. More details are discussed in the article by Liu et al. on page 831–836.
A practical approach to the asymmetric synthesis of the ring A substructure of genkwadane A, a daphnane diterpenoid, was developed. This synthesis features the Mukaiyama aldol reaction to introduce the quaternary stereogenic center at C4 and VO(acac)2‐catalyzed Jackson‐Ellman‐Bolm sulfoxidation to deliver the corresponding sulfoxide. The Dieckmann‐type condensation was efficiently promoted by KHMDS and the ring A substructure was finally accomplished through Barton iodination condition.
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