Expedient synthesis of the tetracyclic core of ent-nakadomarin A.
An efficient eight-step assembly of the tetracyclic core (ABCD rings) of ent-(+)-nakadomarin A, a bioactive hexacyclic marine alkaloid, has been realized with Sonogashira coupling, platinum(II)-promoted cascade cyclizations, and saturation of a challenging carbon-carbon double bond through a hydroboration/oxidation/xanthate formation/Barton-McCombie deoxygenation sequence as key transformations.
Deng
Haibing
H
Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China.
Yang
Xiaobao
X
Tong
Zhaolong
Z
Li
Zhong
Z
Zhai
Hongbin
H
D000818:Animals; D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry
D002243:Carbolines; C476640:nakadomarin A