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An Expedient Approach to the Benzopyran Core: Application to Synthesis of the Natural Products (±)‐Xyloketals and (±)‐Alboatrin
Author(s) -
Xu Zhongliang,
Li Yiying,
Lu Bingtai,
Pang Jiyan,
Lin Yongcheng
Publication year - 2010
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201190018
Subject(s) - chemistry , benzopyran , regioselectivity , yield (engineering) , natural product , ring (chemistry) , core (optical fiber) , unit (ring theory) , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , mathematics , materials science , mathematics education , metallurgy , composite material
A mild and efficient protocol for the synthesis of the benzopyran ring has been described and a series of chromans compounds is reported, the yield is from 72% to 95%. The diadduct tended to angular product and showed good regioselectivity. This strategy was applied for the benzopyran derived natural products (±)‐xyloketals and (±)‐alboatrin. The crystal of compound 9 exhibited centro‐symmetric space group, containing two isomers in one unit. The relative configurations were 1 R ,10 R ,15 S and 34 S ,22 R ,30 S , respectively.