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. 2020 Nov 6;22(21):8714-8719.
doi: 10.1021/acs.orglett.0c03308. Epub 2020 Oct 19.

Total Synthesis of Meayamycin and O-Acyl Analogues

Christopher Gartshore  1 , Shinji Tadano  1 , Prem B Chanda  1 , Anindya Sarkar  1 , Naidu S Chowdari  2 , Sanjeev Gangwar  2 , Qian Zhang  2 , Gregory D Vite  2   3 , Jelena Momirov  1 , Dale L Boger  1
Affiliations

Total Synthesis of Meayamycin and O-Acyl Analogues

Christopher Gartshore et al. Org Lett. .

Abstract

A short, scalable total synthesis of meayamycin is described by an approach that entails a longest linear sequence of 12 steps (22 steps overall) from commercially available chiral pool materials (ethyl l-lactate, BocNH-Thr-OH, and d-ribose) and introduces the most straightforward preparation of the right-hand subunit detailed to date. The use of the approach in the divergent synthesis of a representative series of O-acyl analogues is exemplified.

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Figures

Figure 1.
Figure 1.
Target structures, key intermediates, and chiral pool starting materials.
Figure 2.
Figure 2.
O-Acyl analogues, synthesis and activity.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4
Scheme 5
Scheme 5
See this image and copyright information in PMC

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