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A concise and unified strategy for synthesis of the C1-C18 macrolactone fragments of FD-891, FD-892 and their analogues: formal total synthesis of FD-891.
Org Lett. 2014 Oct 03; 16(19):5216-9.OL

Abstract

A concise and unified strategy for the synthesis of C1-C18 macrolactone fragments of FD-891 and FD-892 as well as their analogues is reported. The strategy includes a stereoselective vinylogous Mukaiyama aldol reaction (VMAR) using chiral silyl ketene N,O-acetal to construct C6-C7 stereocenters, an E-selective ring closing metathesis to construct a C12-C13 olefin, and stereodivergent construction of a C8-C9 epoxide.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Kanoh N
Graduate School of Pharmaceutical Sciences and ‡Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University , 6-3 Aza-Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan.
Kawamata A
No affiliation info available
Itagaki T
No affiliation info available
Miyazaki Y
No affiliation info available
Yahata K
No affiliation info available
Kwon E
No affiliation info available
Iwabuchi Y
No affiliation info available

MeSH

AldehydesLactonesMacrolidesMolecular StructureStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

25247478

Citation

Kanoh, Naoki, et al. "A Concise and Unified Strategy for Synthesis of the C1-C18 Macrolactone Fragments of FD-891, FD-892 and Their Analogues: Formal Total Synthesis of FD-891." Organic Letters, vol. 16, no. 19, 2014, pp. 5216-9.
Kanoh N, Kawamata A, Itagaki T, et al. A concise and unified strategy for synthesis of the C1-C18 macrolactone fragments of FD-891, FD-892 and their analogues: formal total synthesis of FD-891. Org Lett. 2014;16(19):5216-9.
Kanoh, N., Kawamata, A., Itagaki, T., Miyazaki, Y., Yahata, K., Kwon, E., & Iwabuchi, Y. (2014). A concise and unified strategy for synthesis of the C1-C18 macrolactone fragments of FD-891, FD-892 and their analogues: formal total synthesis of FD-891. Organic Letters, 16(19), 5216-9. https://doi.org/10.1021/ol502633j
Kanoh N, et al. A Concise and Unified Strategy for Synthesis of the C1-C18 Macrolactone Fragments of FD-891, FD-892 and Their Analogues: Formal Total Synthesis of FD-891. Org Lett. 2014 Oct 3;16(19):5216-9. PubMed PMID: 25247478.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A concise and unified strategy for synthesis of the C1-C18 macrolactone fragments of FD-891, FD-892 and their analogues: formal total synthesis of FD-891. AU - Kanoh,Naoki, AU - Kawamata,Ayano, AU - Itagaki,Tomohiro, AU - Miyazaki,Yuta, AU - Yahata,Kenzo, AU - Kwon,Eunsang, AU - Iwabuchi,Yoshiharu, Y1 - 2014/09/23/ PY - 2014/9/24/entrez PY - 2014/9/24/pubmed PY - 2014/12/15/medline SP - 5216 EP - 9 JF - Organic letters JO - Org Lett VL - 16 IS - 19 N2 - A concise and unified strategy for the synthesis of C1-C18 macrolactone fragments of FD-891 and FD-892 as well as their analogues is reported. The strategy includes a stereoselective vinylogous Mukaiyama aldol reaction (VMAR) using chiral silyl ketene N,O-acetal to construct C6-C7 stereocenters, an E-selective ring closing metathesis to construct a C12-C13 olefin, and stereodivergent construction of a C8-C9 epoxide. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/25247478/A_concise_and_unified_strategy_for_synthesis_of_the_C1_C18_macrolactone_fragments_of_FD_891_FD_892_and_their_analogues:_formal_total_synthesis_of_FD_891_ DB - PRIME DP - Unbound Medicine ER -