Scalable synthesis of the C14–C23 fragment of Eribulin and Halichondrin B

A novel, scalable approach to the C14–C23 fragment of eribulin mesylate is disclosed. Key 2,3‐Wittig rearrangement is strategically effected via [Rh] mediated decomposition of 1,2,3‐triazole intermediate to derive the 2,5‐trans‐tetrahydrofuran motif, enabling multi‐kilogram access to the desired C14...

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Published in:Bulletin of the Korean Chemical Society 2022-12, Vol.43 (12), p.1367-1372
Main Authors: Kim, U Bin, Samala, Srinivas, Kim, Namhyeon, Bogonda, Ganganna, Lago‐Santomé, Hugo, Jeong, Youngdo, Kim, Jin, Jung, Jaehun, Jeon, Sung‐Hyun, Lee, Seung Jong, Shin, Hyunik
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Language:English
Subjects:
carbene
eribulin
Halichondrin B
rhodium (II) catalysis
stereoselectivity
Wittig rearrangement
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cited_by cdi_FETCH-LOGICAL-c2034-89e9b67ca1b1e444a7a29ffbfe5ef9d1e06e6d859678c8caab56d2e6e88722003
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container_end_page 1372
container_issue 12
container_start_page 1367
container_title Bulletin of the Korean Chemical Society
container_volume 43
creator Kim, U Bin
Samala, Srinivas
Kim, Namhyeon
Bogonda, Ganganna
Lago‐Santomé, Hugo
Jeong, Youngdo
Kim, Jin
Jung, Jaehun
Jeon, Sung‐Hyun
Lee, Seung Jong
Shin, Hyunik
description A novel, scalable approach to the C14–C23 fragment of eribulin mesylate is disclosed. Key 2,3‐Wittig rearrangement is strategically effected via [Rh] mediated decomposition of 1,2,3‐triazole intermediate to derive the 2,5‐trans‐tetrahydrofuran motif, enabling multi‐kilogram access to the desired C14–C23 fragment. A novel approach to the C14–C23 fragment of eribulin mesylate is disclosed. Key 2,3‐Wittig rearrangement is strategically affected via [Rh] mediated decomposition of 1,2,3‐triazole intermediate to derive the 2,5‐trans‐tetrahydrofuran motif, enabling multi‐kilogram access to the desired C14–C23 fragment.
doi_str_mv 10.1002/bkcs.12624
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subjects carbene
eribulin
Halichondrin B
rhodium (II) catalysis
stereoselectivity
Wittig rearrangement
title Scalable synthesis of the C14–C23 fragment of Eribulin and Halichondrin B
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