Synthetic efforts on the road to marine natural products bearing 4-O-2,3,4,6-tetrasubstituted THPs: an update

Fariña-Ramos, Marta; García, Celina; Martı́n, Victor S.; Álvarez-Méndez, Sergio J.

doi:10.1039/d0ra10755g

Cited by 3 publications

(1 citation statement)

References 202 publications

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“…Although the unsaturated side chains of the meliponamycins are less complex than other natural products of the same class, the stereoselective construction of the tetrahydropyran ring is still far from trivial. − It took several attempts until an activated dihydropyran derivative A , suitable for coupling, could be obtained via a Julia–Lythgoe-type addition of deprotonated sulfone C onto chiral aldehyde B followed by oxidation, desulfonation, deprotection (PMB cleavage), and water elimination (Scheme A). The stereogenic centers of the starting materials B and C were introduced via Sharpless dihydroxylation and Sharpless epoxidation/epoxide opening, respectively .…”

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Stereoselective Synthesis of a Protected Side Chain of Meliponamycin A

Andler

Kazmaier

2022

Org. Lett.

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The Matteson homologation was found to be a versatile tool for the construction of the linear polyketide side chain of meliponamycin and related compounds in only four steps. The ester dienolate version of this reaction allowed the introduction of the unsaturated ester moiety in a highly stereoselective fashion. Boronate oxidation/deoxygenation and Sharpless dihydroxylation are additional key steps in the stereoselective construction of this highly functionalized tetrahydropyran ring system, which is characteristic of this substance class.

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Stereoselective Synthesis of a Protected Side Chain of Meliponamycin A

Andler

Kazmaier

2022

Org. Lett.

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N‐Oxide‐Catalyzed Six‐Membered Ring Bromo‐Etherification of ϵ‐Alkenyl Alcohols

Hoshino,

Kasahara,

Marushima

et al. 2024

Adv Synth Catal

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A six‐membered ring bromo‐etherification of ε‐alkenyl alcohols using N‐oxide catalyst was developed to furnish 2‐bromomethyl‐6‐substituted tetrahydropyrans with cis‐selectivity and 3‐bromomethyl isochromans in high yields. DFT calculations indicate that the NMO catalyst enhances the electrophilicity of the bromine atom on NBS via two hydrogen‐bonding interactions after the formation of the NMO‐NBS complex.

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