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Unambiguous assignment of 13C chemical shifts of some hopane and migrated hopane derivatives by 2D NMR

✍ Scribed by Ajit K. Chakravarty; Kazuo Masuda; Hideki Suzuki; Hiroyuki Ageta


Book ID
104204309
Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
696 KB
Volume
50
Category
Article
ISSN
0040-4020

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✦ Synopsis


1% NMR chemical shifts of some migrated hopane derivatives, viz. boehmeryl acetate (l), neohop-13(18)-en-35-ol (2) neomotiol (3), arborinol (4), isoarborinyl acetate ( ) fernenol (6) fernenyl acetate (7) and simiarenol (6), and a hopane derivative, hop-l 7(21)-en-35yl acetate ( ) have been assigned unambiguously on the basis of detailed 20 NMR analyses. Heteronuclear Multiple Bond Correlation (HMBC) spectrum was found to be most informative not only in the assignment of signals to specific carbons but also in the elucidation of back-bone structure of triterpenoids. The relative stereochemistry of most of the chiral centres of the back-bone could also be established from the NOESY spectra.

2866

A.K. CHAKRAVARTY etal.

simiarenol (8)* and hop-l 7(21)-en-3J3-yl acetate [g)s, whose 1% NMR data are not known so far. in the process, 1H NMR signals of methyl protons in particular have also been assigned.

Assignments of lsC NMR chemical shifts for l-9 are summarized in Table and those of 1 H chemical shii particularly of methyl proton8 of l-9 are listed in Tables 2-l 0. 7 FkOAc = , 5 ,-" o


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