Total synthesis of huperserratines A and B

Huperserratines A (1) and B (2), two novel macrocyclic Lycopodium alkaloids, possess an aza-12-membered ring. Here, we describe the first total synthesis of these two natural products in 12 steps. Key elements of the synthesis include the Suzuki-Miyaura coupling, the Hosomi-Sakurai reaction, ring-cl...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 9; no. 14; pp. 3664 - 3668
Main Authors Deng, Zhen-Tao, Wu, Xing-De, Yuan, Zai-Feng, Yu, Nai-Rong, Ou, Yu-Fei, Zhao, Qin-Shi
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 12.07.2022
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Organic
Forging
Metathesis
Natural products
Organic chemistry
Oxidation
Physical Sciences
Scale (corrosion)
Science & Technology
OXIDATION
ALKENES
LYCOPODIUM ALKALOIDS
HUPERZINE
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Summary:Huperserratines A (1) and B (2), two novel macrocyclic Lycopodium alkaloids, possess an aza-12-membered ring. Here, we describe the first total synthesis of these two natural products in 12 steps. Key elements of the synthesis include the Suzuki-Miyaura coupling, the Hosomi-Sakurai reaction, ring-closing metathesis, dihydroxylation, and the Swern oxidation. A gram-scale ring-closing metathesis was pivotal in forging the challenging aza-12-membered ring. This total synthesis would enable future studies on the structure-activity relationship of 1 and 2.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d2qo00608a