A common and versatile synthetic route to (-) and (+) pentenomycin I, (+) halopentenomycin I and dehydropentenomycin.
A versatile and stereoselective total synthesis of (+) and (-) pentenomycin I, (+) halopentenomycins I and dehydropentenomycin from a common chiral polyhydroxylated cyclopentene through oxidation and protection/deprotection has been described. Stereoselective hydroxymethylation, stereoselective Grignard reaction and ring closing metathesis are the key features of our approach.
Indian Institute of Technology Bhubaneswar, School of Basic Sciences, Bhubaneswar, Orissa 751007, India.
Sulagna
S
Das
Indian Institute of Technology Bhubaneswar, School of Basic Sciences, Bhubaneswar, Orissa 751007, India.
Amarendra
A
Panda
Indian Institute of Technology Bhubaneswar, School of Basic Sciences, Bhubaneswar, Orissa 751007, India. Electronic address: spal@iitbbs.ac.in.
Shantanu
S
Pal
D060326:Chemistry Techniques, Synthetic; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D012266:Ribose / Q000737:chemistry; D013237:Stereoisomerism
D003517:Cyclopentanes; C008792:pentenomycin I; D012266:Ribose
Cyclopentenones; Grignard reaction; Halopentenomycin; Ring closing metathesis; Stereoselectivity; d-Ribose