A flexible enantioselective total synthesis of diospongins A and B and their enantiomers using catalytic hetero-Diels-Alder/Rh-catalyzed 1,4-addition and asymmetric transfer hydrogenation reactions as key steps.
A unified enantioselective route to total synthesis of diospongins A and B and their enantiomers has been developed employing achiral starting materials. All three stereocenters were introduced by means of catalytic reactions.
Kumaraswamy
Gullapalli
G
Organic Division-III, Indian Institute of Chemical Technology, Hyderabad, 500 007, India. gkswamy_iict@yahoo.co.in
Ramakrishna
Gajula
G
Naresh
Police
P
Jagadeesh
Bharatam
B
Sridhar
Balasubramanian
B
D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
D011714:Pyrans; C521317:diospongin A; C521318:diospongin B; D006859:Hydrogen