Details
| Original language | English |
|---|---|
| Pages (from-to) | 973-978 |
| Number of pages | 6 |
| Journal | SYNLETT |
| Volume | 35 |
| Issue number | 9 |
| Early online date | 30 Oct 2023 |
| Publication status | Published - 2024 |
Abstract
The [4+1] cyclization of a sugar-based epoxytosylate with various C1 dianion equivalents provide highly functionalized homochiral cyclopentane derivatives. For these, a follow-up chemistry was developed to provide various cyclopentane building blocks as starting points for natural product syntheses. The [4+1] domino protocol relies on a 1,4-Brook rearrangement, which is essential for generating the second carbanion.
Keywords
- Brook rearrangements, cyclizations, domino reactions, ex-chiral pool synthesis, prostaglandins
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
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In: SYNLETT, Vol. 35, No. 9, 2024, p. 973-978.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - [4+1] Cyclizations to Enantiopure Multifunctional Cyclopentanes from d -Glucose Using Formyl Dianion Synthons
AU - Kirschning, Andreas
AU - Schaumann, Ernst
AU - Bräuer, Nico
AU - Michel, Tycho
AU - Oelze, Silke
N1 - Publisher Copyright: © 2024 Georg Thieme Verlag. All rights reserved.
PY - 2024
Y1 - 2024
N2 - The [4+1] cyclization of a sugar-based epoxytosylate with various C1 dianion equivalents provide highly functionalized homochiral cyclopentane derivatives. For these, a follow-up chemistry was developed to provide various cyclopentane building blocks as starting points for natural product syntheses. The [4+1] domino protocol relies on a 1,4-Brook rearrangement, which is essential for generating the second carbanion.
AB - The [4+1] cyclization of a sugar-based epoxytosylate with various C1 dianion equivalents provide highly functionalized homochiral cyclopentane derivatives. For these, a follow-up chemistry was developed to provide various cyclopentane building blocks as starting points for natural product syntheses. The [4+1] domino protocol relies on a 1,4-Brook rearrangement, which is essential for generating the second carbanion.
KW - Brook rearrangements
KW - cyclizations
KW - domino reactions
KW - ex-chiral pool synthesis
KW - prostaglandins
UR - http://www.scopus.com/inward/record.url?scp=85175852990&partnerID=8YFLogxK
U2 - 10.1055/a-2201-3861
DO - 10.1055/a-2201-3861
M3 - Article
AN - SCOPUS:85175852990
VL - 35
SP - 973
EP - 978
JO - SYNLETT
JF - SYNLETT
SN - 0936-5214
IS - 9
ER -