2009
DOI: 10.1021/jo9000405
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(+)- and (−)-Mutisianthol: First Total Synthesis, Absolute Configuration, and Antitumor Activity

Abstract: The first synthesis of the natural product (+)-mutisianthol was accomplished in 11 steps and in 21% overall yield from 2-methylanisole. The synthesis of its enantiomer was also performed in a similar overall yield. The absolute configuration of the sesquiterpene (+)-mutisianthol was assigned as (1S,3R). Key steps in the route are the asymmetric hydrogenation of a nonfunctionalized olefin using chiral iridium catalysts and the ring contraction of 1,2-dihydronaphthalenes using thallium(III) or iodine(III). The t… Show more

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Cited by 85 publications
(40 citation statements)
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“…20 Cross-coupling of 1-chloro-1,2,3,4-tetrahydronaphthalene ( 9 ) with commercially available iodobenzene 10 provides chiral tetrahydronaphthalene ( 11 ) in 70% yield, and 84% ee. Benzylic oxidation of 11 using 3 equiv of CrO 3 in AcOH/H 2 O 21 afforded tetralone 12 in 51% yield (unoptimized) with no erosion of ee. 22 Tetralone 12 is a known intermediate in the synthesis of sertraline.…”
mentioning
confidence: 99%
“…20 Cross-coupling of 1-chloro-1,2,3,4-tetrahydronaphthalene ( 9 ) with commercially available iodobenzene 10 provides chiral tetrahydronaphthalene ( 11 ) in 70% yield, and 84% ee. Benzylic oxidation of 11 using 3 equiv of CrO 3 in AcOH/H 2 O 21 afforded tetralone 12 in 51% yield (unoptimized) with no erosion of ee. 22 Tetralone 12 is a known intermediate in the synthesis of sertraline.…”
mentioning
confidence: 99%
“…We developed a protocol for the synthesis of trans ‐1,3‐disubstituted indanes through thallium(III)10a,e‐ or iodine(III)10b,c‐mediated ring contraction10e–g of 1,2‐dihydronaphthalenes. This reaction was applied in the synthesis of (±)‐ trans ‐trikentrin A9a and of other small molecules 10c,d,h. In this context, we describe herein the first asymmetric synthesis of (+)‐ trans ‐trikentrin A, using an enzymatic resolution and a ring‐contraction reaction as key steps.…”
Section: Introductionmentioning
confidence: 99%
“…The power of iridium-catalyzed asymmetric hydrogenation has been demonstrated in the enantioselective synthesis of several biologically important natural products, such as (+)-and (−)-Mutisianthol, [30] (R)-(+)-7-demethyl-2-methoxycalamenene, [31] Macrocidin A, [32] (−)-Spongidepsin, [33] and (+)-Torrubiellone C. [34] Herein we would like to highlight our contribution to the formal synthesis of Platensimycin (Fig. 5) in collaboration with the Mulzer group.…”
Section: Applications In the Synthesis Of Complex Moleculesmentioning
confidence: 99%