Total synthesis of (+)-tubelactomicin A. 1. Stereoselective synthesis of the lower-half segment by an intramolecular Diels-Alder approach

Toru Motozaki, Kiyoto Sawamura, Akari Suzuki, Keigo Yoshida, Tatsuo Ueki, Aiko Ohara, Ryosuke Munakata, Kenichi Takao, Kin Ichi Tadano

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

(Chemical Equation Presented) Starting from diethyl (R)-malate, synthesis of the lower-half segment of (+)-tubelactomicin A, a 16-membered macrolide antibiotic, has been achieved. The synthesis involved the highly endo- and π-facial selective intramolecular Diels-Alder reaction achieved using a trisubstituted methacrolein derivative tethering a 10-carbon dienyne unit at the β-carbon, which in turn was prepared from a known allylated malic acid derivative.

Original languageEnglish
Pages (from-to)2261-2264
Number of pages4
JournalOrganic Letters
Volume7
Issue number11
DOIs
Publication statusPublished - 2005 May 26

Fingerprint

Carbon
tethering
Derivatives
Diels-Alder reactions
antibiotics
carbon
Macrolides
Cycloaddition Reaction
synthesis
Anti-Bacterial Agents
acids
tubelactomicin A
malic acid
methacrylaldehyde
diethyl malate

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Total synthesis of (+)-tubelactomicin A. 1. Stereoselective synthesis of the lower-half segment by an intramolecular Diels-Alder approach. / Motozaki, Toru; Sawamura, Kiyoto; Suzuki, Akari; Yoshida, Keigo; Ueki, Tatsuo; Ohara, Aiko; Munakata, Ryosuke; Takao, Kenichi; Tadano, Kin Ichi.

In: Organic Letters, Vol. 7, No. 11, 26.05.2005, p. 2261-2264.

Research output: Contribution to journalArticle

Motozaki, T, Sawamura, K, Suzuki, A, Yoshida, K, Ueki, T, Ohara, A, Munakata, R, Takao, K & Tadano, KI 2005, 'Total synthesis of (+)-tubelactomicin A. 1. Stereoselective synthesis of the lower-half segment by an intramolecular Diels-Alder approach', Organic Letters, vol. 7, no. 11, pp. 2261-2264. https://doi.org/10.1021/ol0507625
Motozaki, Toru ; Sawamura, Kiyoto ; Suzuki, Akari ; Yoshida, Keigo ; Ueki, Tatsuo ; Ohara, Aiko ; Munakata, Ryosuke ; Takao, Kenichi ; Tadano, Kin Ichi. / Total synthesis of (+)-tubelactomicin A. 1. Stereoselective synthesis of the lower-half segment by an intramolecular Diels-Alder approach. In: Organic Letters. 2005 ; Vol. 7, No. 11. pp. 2261-2264.
@article{a5ff47e0924a4721b84a9cf7a65f47ad,
title = "Total synthesis of (+)-tubelactomicin A. 1. Stereoselective synthesis of the lower-half segment by an intramolecular Diels-Alder approach",
abstract = "(Chemical Equation Presented) Starting from diethyl (R)-malate, synthesis of the lower-half segment of (+)-tubelactomicin A, a 16-membered macrolide antibiotic, has been achieved. The synthesis involved the highly endo- and π-facial selective intramolecular Diels-Alder reaction achieved using a trisubstituted methacrolein derivative tethering a 10-carbon dienyne unit at the β-carbon, which in turn was prepared from a known allylated malic acid derivative.",
author = "Toru Motozaki and Kiyoto Sawamura and Akari Suzuki and Keigo Yoshida and Tatsuo Ueki and Aiko Ohara and Ryosuke Munakata and Kenichi Takao and Tadano, {Kin Ichi}",
year = "2005",
month = "5",
day = "26",
doi = "10.1021/ol0507625",
language = "English",
volume = "7",
pages = "2261--2264",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "11",

}

TY - JOUR

T1 - Total synthesis of (+)-tubelactomicin A. 1. Stereoselective synthesis of the lower-half segment by an intramolecular Diels-Alder approach

AU - Motozaki, Toru

AU - Sawamura, Kiyoto

AU - Suzuki, Akari

AU - Yoshida, Keigo

AU - Ueki, Tatsuo

AU - Ohara, Aiko

AU - Munakata, Ryosuke

AU - Takao, Kenichi

AU - Tadano, Kin Ichi

PY - 2005/5/26

Y1 - 2005/5/26

N2 - (Chemical Equation Presented) Starting from diethyl (R)-malate, synthesis of the lower-half segment of (+)-tubelactomicin A, a 16-membered macrolide antibiotic, has been achieved. The synthesis involved the highly endo- and π-facial selective intramolecular Diels-Alder reaction achieved using a trisubstituted methacrolein derivative tethering a 10-carbon dienyne unit at the β-carbon, which in turn was prepared from a known allylated malic acid derivative.

AB - (Chemical Equation Presented) Starting from diethyl (R)-malate, synthesis of the lower-half segment of (+)-tubelactomicin A, a 16-membered macrolide antibiotic, has been achieved. The synthesis involved the highly endo- and π-facial selective intramolecular Diels-Alder reaction achieved using a trisubstituted methacrolein derivative tethering a 10-carbon dienyne unit at the β-carbon, which in turn was prepared from a known allylated malic acid derivative.

UR - http://www.scopus.com/inward/record.url?scp=20444505606&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=20444505606&partnerID=8YFLogxK

U2 - 10.1021/ol0507625

DO - 10.1021/ol0507625

M3 - Article

VL - 7

SP - 2261

EP - 2264

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 11

ER -