Details
| Original language | English |
|---|---|
| Pages (from-to) | 1127-1133 |
| Number of pages | 7 |
| Journal | SYNLETT |
| Volume | 28 |
| Issue number | 10 |
| Publication status | Published - Jun 2017 |
Abstract
The chemical synthesis of secosterols is an arena for the application of C-H functionalization methods as well as C-C manipulations. Studies on the innate reactivity of synthetic intermediates to undergo C-C scissions and rearrangements can shed light on biosynthetic pathways, or, provide proof for biosynthetic proposals. Examples of the authors work (synthesis of the 14,15-secosterol strophasterol A), as well as examples from current literature (Tian's synthetic work on 13,14:14,15-disecosterols glaucogenins C and D, and Baran's synthesis of 9,10-secosterol cortistatin A) are discussed. 1 Introduction 2 The Synthesis of Strophasterol A Employing the Concept of Innate Reactivity 3 Synthetic Work in the Glaucogenin Family of Natural Products 4 The Synthesis of Cortistatin A Using a Radical Ring Expansion 5 Conclusion.
Keywords
- C-C manipulation, C-H oxidation, cortistatin, glaucogenin, secosterols, strophasterol, synthetic strategies
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
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In: SYNLETT, Vol. 28, No. 10, 06.2017, p. 1127-1133.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Synthesis of Secosterols as an Arena for C-H Functionalization and C-C Manipulation Tactics
AU - Heinze, Robert C.
AU - Heretsch, Philipp
N1 - Publisher Copyright: © 2017 Georg Thieme Verlag KG Stuttgart · New York.
PY - 2017/6
Y1 - 2017/6
N2 - The chemical synthesis of secosterols is an arena for the application of C-H functionalization methods as well as C-C manipulations. Studies on the innate reactivity of synthetic intermediates to undergo C-C scissions and rearrangements can shed light on biosynthetic pathways, or, provide proof for biosynthetic proposals. Examples of the authors work (synthesis of the 14,15-secosterol strophasterol A), as well as examples from current literature (Tian's synthetic work on 13,14:14,15-disecosterols glaucogenins C and D, and Baran's synthesis of 9,10-secosterol cortistatin A) are discussed. 1 Introduction 2 The Synthesis of Strophasterol A Employing the Concept of Innate Reactivity 3 Synthetic Work in the Glaucogenin Family of Natural Products 4 The Synthesis of Cortistatin A Using a Radical Ring Expansion 5 Conclusion.
AB - The chemical synthesis of secosterols is an arena for the application of C-H functionalization methods as well as C-C manipulations. Studies on the innate reactivity of synthetic intermediates to undergo C-C scissions and rearrangements can shed light on biosynthetic pathways, or, provide proof for biosynthetic proposals. Examples of the authors work (synthesis of the 14,15-secosterol strophasterol A), as well as examples from current literature (Tian's synthetic work on 13,14:14,15-disecosterols glaucogenins C and D, and Baran's synthesis of 9,10-secosterol cortistatin A) are discussed. 1 Introduction 2 The Synthesis of Strophasterol A Employing the Concept of Innate Reactivity 3 Synthetic Work in the Glaucogenin Family of Natural Products 4 The Synthesis of Cortistatin A Using a Radical Ring Expansion 5 Conclusion.
KW - C-C manipulation
KW - C-H oxidation
KW - cortistatin
KW - glaucogenin
KW - secosterols
KW - strophasterol
KW - synthetic strategies
UR - http://www.scopus.com/inward/record.url?scp=85014710046&partnerID=8YFLogxK
U2 - 10.1055/s-0036-1588745
DO - 10.1055/s-0036-1588745
M3 - Article
VL - 28
SP - 1127
EP - 1133
JO - SYNLETT
JF - SYNLETT
SN - 0936-5214
IS - 10
ER -