Enantioselective total synthesis of marine diterpenoid clavulactone.
The key steps in the synthesis of clavulactone are formation of an enantiopure cyclopentane precursor by epoxide rearrangement and intramolecular carbonyl-ene reaction, construction of the 3,4-dihydro-2H-pyran ring by intermolecular hetero-Diels-Alder reaction, closure of the eleven-membered ring, and finally generation of the lactone functionality by chemoselective allylic C(sp(3))-H oxidation.
State Key Laboratory of Bioorganic and Natural Products, Chemistry, Shanghai Institute of Organic Chemistry, 345 Lingling Road, Shanghai 200032, China.
Zhen-Yu
ZY
Yang
Hong-Ze
HZ
Liao
Kang
K
Sheng
Yong-Fei
YF
Chen
Zhu-Jun
ZJ
Yao
D002384:Catalysis; D004224:Diterpenes / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
D004224:Diterpenes; D007783:Lactones; C438459:clavulactone