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Determination of Absolute Configuration of Decipinone, a Diterpenoid Ester with a Myrsinane‐Type Carbon Skeleton, by NMR Spectroscopy
Author(s) -
Jassbi Amir Reza,
Fukushi Yukiharu,
Tahara Satoshi
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200206)85:6<1706::aid-hlca1706>3.0.co;2-z
Subject(s) - absolute configuration , chemistry , diterpene , carbon skeleton , terpenoid , absolute (philosophy) , stereochemistry , spectroscopy , philosophy , physics , epistemology , quantum mechanics
The absolute configuration of decipinone ( 2 ), a myrsinane‐type diterpene ester previously isolated from Euphorbia decipiens , has been determined by NMR study of its axially chiral derivatives (a R )‐ and (a S )‐ N ‐hydroxy‐2′‐methoxy‐1,1′‐binaphthalene‐2‐carboximidoyl chloride ((a R )‐MBCC ( 3a ) and (a S )‐MBCC ( 3b )). The absolute configurations at C(7) and C(13) of 2 determined were ( R ) and ( S ), respectively. Therefore, considering the relative configuration of 2 , the absolute configuration determined was (2 S ,3 S ,4 R ,5 R ,6 R ,7 R ,11 S ,12 R ,13 S ,15 R ).