2021
DOI: 10.1021/jacs.1c02150
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Total Synthesis and Computational Investigations of Sesquiterpene-Tropolones Ameliorate Stereochemical Inconsistencies and Resolve an Ambiguous Biosynthetic Relationship

Abstract: The sesquiterpene-tropolones belong to a distinctive structural class of meroterpene natural products with impressive biological activities, including anticancer, antifungal, antimalarial, and antibacterial. In this article, we describe a concise, modular, and cycloaddition-based approach to a series of sesquiterpene mono-and bistropolones, including (−)-epolone B, (+)-isoepolone B, (±)-dehydroxypycnidione, and (−)-10-epi-pycnidione. Alongside the development of a general strategy to access this unique family … Show more

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Cited by 40 publications
(35 citation statements)
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“…Only few examples to date depict the applicability of β-caryophyllene and β-caryophyllene oxide in gram-scale syntheses of natural products of rare occurrence. 11,12…”
Section: Introductionmentioning
confidence: 99%
See 1 more Smart Citation
“…Only few examples to date depict the applicability of β-caryophyllene and β-caryophyllene oxide in gram-scale syntheses of natural products of rare occurrence. 11,12…”
Section: Introductionmentioning
confidence: 99%
“…Only few examples to date depict the applicability of β-caryophyllene and β-caryophyllene oxide in gramscale syntheses of natural products of rare occurrence. 11,12 Our ongoing research in the field of natural product semisynthesis from β-caryophyllene has resulted in the convergent biomimetic gram-scale synthesis of rumphellolide J (7) 2 by esterification of rumphellaoic acid A (5) 13,14 and 4β,8β-epoxycaryophyllan-5-ol (6) 15,16 (Scheme 1).…”
Section: Introductionmentioning
confidence: 99%
“…xenovulene A 1, neosetophomone B 2, pycnidione 3, eupenifeldin 4; Scheme 1 A) possess potent psychoactive, antitumor and antiarthritic properties. [1][2][3][4][5] All TS feature a core 11-membered macrocycle that is derived from the sesquiterpene humulene. [6,7] The biosynthesis of TS proceeds via a core intermolecular hetero Diels-Alder reaction that connects humulene with the polyketidederived tropolone nucleus observed in 1-4 (Electronic Supplementary Information [ESI] Figure S1-S2).…”
mentioning
confidence: 99%
“…The Sarlah group's interest in hetero-Diels-Alder reactions and meroterpenoids culminated in biomimetic and modular total syntheses of two naturally occurring tropolones; (-)-epolone B (188) and (±)-dehydroxypycnidione (189) (Scheme 20). 31 Both compounds share a common 11-membered core but differ in the number of attached tropolone moieties. It was envisioned that these two compounds could be prepared through the union of a tropolone-derived ortho-quinone methide and α-humulene (12) (or its 10-hydroxy derivative 193).…”
Section: Sarlah's Total Synthesis Of (-)-Epolone B and (±)-Dehydroxypycnidionementioning
confidence: 99%