Details
| Original language | English |
|---|---|
| Number of pages | 46 |
| Journal | SYNLETT |
| Volume | 34 |
| Early online date | 30 Oct 2023 |
| Publication status | Published - 30 Nov 2023 |
Abstract
The [4+1] cyclizations of a sugar-based epoxytosylate with various C1 dianion equivalents provides highly functionalized homochiral cyclopentanes. 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 the generation of 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. 34, 30.11.2023.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - 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
PY - 2023/11/30
Y1 - 2023/11/30
N2 - The [4+1] cyclizations of a sugar-based epoxytosylate with various C1 dianion equivalents provides highly functionalized homochiral cyclopentanes. 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 the generation of the second carbanion.
AB - The [4+1] cyclizations of a sugar-based epoxytosylate with various C1 dianion equivalents provides highly functionalized homochiral cyclopentanes. 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 the generation of 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 - 34
JO - SYNLETT
JF - SYNLETT
SN - 0936-5214
ER -