Totalsynthese des antifungalen Wirkstoffs Echinocandin C

Abstract2‐Propargyl alcohols are widely used in organic reactions. Their great success is rooted in the presence of multiple functional groups. This review will focus on six types of mechanisms: (i) 2‐propargyl alcohols as carbocation precursors, (ii) alkynes as electrophiles, (iii) alcohols as nucleophiles, (iv) fracture via ketones or elimination into alkene intermediates, (v) oxidation into alkynyl‐ortho‐quinone methides or carbonyl intermediates, and (vi) ring expansions. Reactions involving alkanes, alkenes, alkynes, arenes, alcohols, amines, amides, ketones, CO2, hydrazine, iodobenzene, azides, carbenes, arylboronic acids, etc. will be discussed. We hope that this review will help to promote future research in this area.magnified image

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2‐Propargyl Alcohols in Organic Synthesis

Qian

Huang

et al. 2019

Adv Synth Catal

137

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Green Late‐Stage Functionalization of Tryptamines

Xu,

Zhang,

Cai

et al. 2024

Chemistry A European J

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An efficient and rapid protocol for the oxidative halogenation of tryptamines with 10% aqueous NaClO has been developed. This reaction is featured by its operational simplicity, metal‐free conditions, no purification, and high yield. Notably, the resulting key intermediates are suitable for further functionalization with various nucleophiles, including amines, N‐aromatic heterocycles, indoles and phenols. The overall transformation exhibits broad functional‐group tolerance and is applicable to the late‐stage functionalization of complex biorelevant molecules.

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Total Synthesis of the Anticancer Marine Natural Product Mycalol

2018

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This communication describes a synthetic study of the originally proposed structure of mycalol (1) and the total synthesis of the actual structure of the anticancer marine natural product mycalol (2). The total synthesis of the originally proposed structure of mycalol (1) was targeted by a late‐stage asymmetric dihydroxylation, which resulted in an inseparable mixture of diastereomers. Thus a new strategy was developed for the total synthesis of the revised structure of mycalol (2); all the stereocentres except the C‐2′‐OH were created in an asymmetric fashion by using a Maruoka allylation, a Noyori asymmetric reduction, and an asymmetric alkynylation.

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Totalsynthese des antifungalen Wirkstoffs Echinocandin C

Cited by 4 publications

References 41 publications

2‐Propargyl Alcohols in Organic Synthesis

2‐Propargyl Alcohols in Organic Synthesis

Green Late‐Stage Functionalization of Tryptamines

Total Synthesis of the Anticancer Marine Natural Product Mycalol

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