Details
| Original language | English |
|---|---|
| Pages (from-to) | 4400-4411 |
| Number of pages | 12 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2015 |
| Issue number | 20 |
| Publication status | Published - 1 Jul 2015 |
Abstract
The tedanolides are biologically active polyketides that exhibit a characteristic feature of an 18-membered macrolactone generated from a primary hydroxyl group. In the realm of polyketides only secondary alcohols are generated by polyketidal transformations. With this knowledge, Taylor hypothesized that the observed macrolactone might arise from an intramolecular transesterification. To investigate this hypothetical transesterification, we completed the synthesis of desepoxy-isotedanolide as tedanolide's putative biosynthetic precursor. This synthesis required a modified protecting group strategy, which proved to be non-trivial. Unfortunately, it was not possible to accomplish the envisioned transesterification under laboratory conditions.
Keywords
- Aldol reactions, Biosynthesis, Macrolides, Natural products, Synthetic methods
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: European Journal of Organic Chemistry, Vol. 2015, No. 20, 01.07.2015, p. 4400-4411.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - The Synthesis of Desepoxy-Isotedanolide - A Potential Biosynthetic Precursor of Tedanolide
AU - Naini, Arun
AU - Fohrer, Jörg
AU - Kalesse, Markus
N1 - Publisher Copyright: © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2015/7/1
Y1 - 2015/7/1
N2 - The tedanolides are biologically active polyketides that exhibit a characteristic feature of an 18-membered macrolactone generated from a primary hydroxyl group. In the realm of polyketides only secondary alcohols are generated by polyketidal transformations. With this knowledge, Taylor hypothesized that the observed macrolactone might arise from an intramolecular transesterification. To investigate this hypothetical transesterification, we completed the synthesis of desepoxy-isotedanolide as tedanolide's putative biosynthetic precursor. This synthesis required a modified protecting group strategy, which proved to be non-trivial. Unfortunately, it was not possible to accomplish the envisioned transesterification under laboratory conditions.
AB - The tedanolides are biologically active polyketides that exhibit a characteristic feature of an 18-membered macrolactone generated from a primary hydroxyl group. In the realm of polyketides only secondary alcohols are generated by polyketidal transformations. With this knowledge, Taylor hypothesized that the observed macrolactone might arise from an intramolecular transesterification. To investigate this hypothetical transesterification, we completed the synthesis of desepoxy-isotedanolide as tedanolide's putative biosynthetic precursor. This synthesis required a modified protecting group strategy, which proved to be non-trivial. Unfortunately, it was not possible to accomplish the envisioned transesterification under laboratory conditions.
KW - Aldol reactions
KW - Biosynthesis
KW - Macrolides
KW - Natural products
KW - Synthetic methods
UR - http://www.scopus.com/inward/record.url?scp=85027947215&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201500568
DO - 10.1002/ejoc.201500568
M3 - Article
AN - SCOPUS:85027947215
VL - 2015
SP - 4400
EP - 4411
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 20
ER -