A practical total synthesis of (+)-spirolaxine methyl ether.
An efficient and practical total synthesis of (+)-spirolaxine methyl ether is described. The phthalide-aldehyde 3 has been prepared via the Diels-Alder reaction between 1,4-unconjugated diene 5 and a long-chain acetylenic dienophile 6. The carbon framework of spiroketal sulfone 4 has been constructed from monobenzyl protected 1,5-pentanediol and the stereochemistry in both the phthalide portion and the spiroketal portion has been established by the Sharpless asymmetric epoxidation.
Division of Organic Chemistry, Discovery Laboratory, Indian Institute of Chemical Technology, Hyderabad, India. yadavpub@iict.res.in
J S
JS
Yadav
M
M
Sreenivas
A
A
Srinivas Reddy
B V
BV
Subba Reddy
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D016480:Helicobacter pylori / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D005663:Furans; D013141:Spiro Compounds; C520774:spiroketal; C517924:spirolaxine methyl ether