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Synthesis of (4 R ,12 S ,15 S ,16 S ,19 R ,20 R ,34 S )‐Muricatetrocin and (4 R ,12 R ,15 S ,16 S ,19 R ,20 R ,34 S )‐Muricatetrocin, Two Potent Inhibitors of Mitochondrial Complex I
Author(s) -
Bäurle Stefan,
Peters Ulf,
Friedrich Thorsten,
Koert Ulrich
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200006)2000:12<2207::aid-ejoc2207>3.0.co;2-c
Subject(s) - chemistry , stereochemistry
Abstract (4 R ,12 S ,15 S ,16 S ,19 R ,20 R ,34 S )‐Muricatetrocin ( 1 ) and (4 R ,12 R ,15 S ,16 S ,19 R ,20 R ,34 S )‐muricatetrocin ( 2 ) were synthesized by a modular synthetic strategy. Both compounds act as potent inhibitors of mitochondrial complex I. Compound 1 showed analytical data in agreement with howiicin E and a fit with the data for muricatetrocin A if one reassigns the reported 13 C signals for C(13) and C(14). Compound 2 matched muricatetrocin B in respect to all NMR data. However, a lower optical rotation was found for 2 ([α] D 28 = +6.7) than was reported for the natural product ([α] D 25 = +15.0).