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First Total Synthesis of Prionoid E, A Bioactive Rearranged Secoabietane Diterpene Quinone from Salvia prionitis
Author(s) -
Deng Fei,
Xu Jun,
Zhao Min,
Liu HongYing,
Ye Yang,
Zhang JinSheng
Publication year - 2011
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/hlca.201000435
Subject(s) - chemistry , diterpene , quinone , total synthesis , aldol condensation , salvia miltiorrhiza , stereochemistry , yield (engineering) , organic chemistry , medicine , materials science , alternative medicine , traditional chinese medicine , pathology , metallurgy , catalysis
The first total synthesis of prionoid E ( 1 ), a rearranged secoabietane diterpene quinone isolated from Salvia prionitis , was achieved efficiently by means of Wacker oxidation ( Scheme 5 ) and aldol condensation ( Scheme 7 ) as the key steps in the synthetic sequence. Thus 1 was prepared in 15 steps in 3.7% yield starting on one hand from anisole (=methoxybenzene) and methylsuccinic anhydride (=dihydro‐3‐methylfuran‐2,5‐dione) via 4 ( Scheme 3 and 5 ), and on the other hand from 2‐hydroxy‐2‐methylpropanoic acid via 5 ( Scheme 6 ).