Iodine-catalyzed highly diastereoselective synthesis of trans-2,6-disubstituted-3,4-dihydropyrans: application to concise construction of C28-C37 bicyclic core of (+)-sorangicin A.
A novel iodine-catalyzed highly diastereoselective synthesis of trans-2,6-disubstituted-3,4-dihydropyrans have been achieved from delta-hydroxy alpha,beta-unsaturated aldehydes by treating with allyltrimethyl silane in THF at room temperature with good to excellent yields. This methodology has been successfully implemented for a concise asymmetric synthesis of C28-C37 dioxabicyclo[3.2.1]octane ring system of (+)-sorangicin A in 8 steps with 21% overall yield.
Mohapatra
Debendra K
DK
Organic Chemistry Division-I, Indian Institute of Chemical Technology, Council of Scientific & Industrial Research (CSIR), Habsiguda, Uppal Road, Hyderabad-500007, India. mohapatra@iict.res.in
Das
Pragna P
PP
Pattanayak
Manas Ranjan
MR
Yadav
J S
JS
D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000617:Aminoglycosides; D001643:Bridged Bicyclo Compounds; D011714:Pyrans; C051799:sorangicin A; D007455:Iodine