Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Divergent Synthesis of Revised Apratoxin E, 30-epi-Apratoxin E, and 30S/30R-Oxoapratoxin E

Divergent Synthesis of Revised Apratoxin E, 30-epi-Apratoxin E, and 30S/30R-Oxoapratoxin E
Guo-Qiang Lin, Bang-Guo Wei, Zhuo-Ya Mao, Chang-Mei Si, Yi-Wen Liu, Han-Qing Dong
In this report, originally proposed apratoxin E (30S-7), revised apratoxin E (30R-7), and (30S)/(30R)-oxoapratoxin E (30S)-38/(30R)-38 were efficiently prepared by two synthetic methods. The chiral lactone 10, recycled from the degradation of saponin glycosides, was utilized to prepare the key nonpeptide fragment 9. Our alternative convergent assembly strategy was applied to the divergent synthesis of revised apratoxin E and its three analogues. Moreover, ring-closing metathesis (RCM) was for the first time found to be an efficient strategy for the macrocyclization of apratoxins.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01598

DOI: 10.1021/acs.joc.7b01598

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