Asymmetric total synthesis of (+)-monocerin

Fang, Bowen; Xie, Xingang; Li, Huilin; Peng, Jing; Gu, Jixiang; She, Xuegong

doi:10.1016/j.tetlet.2013.09.055

Cited by 14 publications

(7 citation statements)

References 24 publications

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“…strains (IO1 and IO2) induced the production of two known compounds norlichexanthone (2) 14 and monocerin (3), 15 which were not detected in either of the axenic fungal controls ( Figure S12). Co-cultivation of microorganisms has repeatedly been shown to induce the formation of compounds that are not detected when the respective microorganisms are grown under axenic conditions.…”

Section: Resultsmentioning

confidence: 99%

A new fusarielin analogue from Penicillium sp. isolated from the Mediterranean sponge Ircinia oros

Chen

Aktas

Konuklugil

et al. 2015

Tetrahedron Letters

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Section: Resultsmentioning

confidence: 99%

A new fusarielin analogue from Penicillium sp. isolated from the Mediterranean sponge Ircinia oros

Chen

Aktas

Konuklugil

et al. 2015

Tetrahedron Letters

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“…The 4-oxyisochroman-1-one skeleton of the fungal metabolite monocerin could be efficiently constructed from potentially bio-based 3,4,5-trimethoxybenzaldehyde over the sequence of 11 reactions with an overall yield of 5% ( Fang et al., 2013 ).…”

Section: Construction Of Natural Products From Potentially Lignin-dermentioning

confidence: 99%

Pharmaceutically relevant (hetero)cyclic compounds and natural products from lignin-derived monomers: Present and perspectives

Afanasenko

Barta

2021

iScience

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Summary Lignin, the richest source of renewable aromatics on the planet, is an intriguing raw material for the construction of value-added aromatics. In the past decade, much progress has been made regarding the development of efficient lignin depolymerization methods, able to produce specific monophenol derivatives in high-enough selectivity and yields. This now serves as an excellent basis for developing powerful downstream conversion strategies toward a wide range of products, including fine chemical building blocks. The inherent structural features of lignin-derived platform chemicals undoubtedly inspire the development of novel, creative, atom-economic synthetic routes toward biologically active molecules or natural products. In this perspective we attempt to bridge the structural features of lignin-derived platform chemicals with existing synthetic strategies toward the construction of heterocycles and provide a summary of efforts for the production of natural products from aromatics that can be, in principle, obtained from lignin. Last, we comment on the latest efforts that present entire value-chains from wood to valuable pharmaceutically relevant compounds.

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“…A concise asymmetric total synthesis of (+)-monocerin ((+)-76) was achieved by the group of She et al via a Lewis acid-mediated stereoselective cyclization reaction (Scheme 16). 168 The synthesis commenced with the conversion of 3,4,5-trimethoxybenzaldehyde ( 61) into an allylic alcohol. Enantioselective epoxidation followed by O-protection afforded compound 72.…”

Section: Wood/ligninmentioning

confidence: 99%