Synthesis of (±)-Marasmic Acid via 1-Oxaspirohexane Rearrangement

Yoshito Tobe; Dai Yamashita; Tohru Takahashi; Masashi Inata; Jun ichi Sato; Kiyomi Kakiuchi; Kazuya Kobiro; Yoshinobu Odaira

doi:10.1021/ja00158a042

Synthesis of (±)-Marasmic Acid via 1-Oxaspirohexane Rearrangement

Yoshito Tobe^*, Dai Yamashita, Tohru Takahashi, Masashi Inata, Jun ichi Sato, Kiyomi Kakiuchi, Kazuya Kobiro, Yoshinobu Odaira

^*此作品的通信作者

應用化學系

研究成果: Article › 同行評審

37 引文斯高帕斯（Scopus）

摘要

A formal total synthesis of marasmic acid (1), an antimicrobial sesquiterpene, has been achieved in a stereoselective manner from known enone 9. The initial key step involves stereo-and regioselective photocycloaddition of aliene to enone 8. The most important strategic transformation in this synthesis is the acid-catalyzed rearrangement of 1-oxaspirohexane 7 to lactone 6 having a norcarane skeleton with an appendage suitable for further manipulation. Finally, Sharpless allylic oxidation followed by Swern oxidation of hydroxy ester 24 provided a route to methyl marasmate (5).

原文	English
頁（從 - 到）	775-779
頁數	5
期刊	Journal of the American Chemical Society
卷	112
發行號	2
DOIs	https://doi.org/10.1021/ja00158a042
出版狀態	Published - 1 1月 1990

存取文件

10.1021/ja00158a042

其它文件與鏈接

Link to publication in Scopus

引用此

@article{4da453a00e3043f38f20f6e7de01bbdb,

title = "Synthesis of (±)-Marasmic Acid via 1-Oxaspirohexane Rearrangement",

abstract = "A formal total synthesis of marasmic acid (1), an antimicrobial sesquiterpene, has been achieved in a stereoselective manner from known enone 9. The initial key step involves stereo-and regioselective photocycloaddition of aliene to enone 8. The most important strategic transformation in this synthesis is the acid-catalyzed rearrangement of 1-oxaspirohexane 7 to lactone 6 having a norcarane skeleton with an appendage suitable for further manipulation. Finally, Sharpless allylic oxidation followed by Swern oxidation of hydroxy ester 24 provided a route to methyl marasmate (5).",

author = "Yoshito Tobe and Dai Yamashita and Tohru Takahashi and Masashi Inata and Sato, {Jun ichi} and Kiyomi Kakiuchi and Kazuya Kobiro and Yoshinobu Odaira",

year = "1990",

month = jan,

day = "1",

doi = "10.1021/ja00158a042",

language = "English",

volume = "112",

pages = "775--779",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "2",

}

TY - JOUR

T1 - Synthesis of (±)-Marasmic Acid via 1-Oxaspirohexane Rearrangement

AU - Tobe, Yoshito

AU - Yamashita, Dai

AU - Takahashi, Tohru

AU - Inata, Masashi

AU - Sato, Jun ichi

AU - Kakiuchi, Kiyomi

AU - Kobiro, Kazuya

AU - Odaira, Yoshinobu

PY - 1990/1/1

Y1 - 1990/1/1

N2 - A formal total synthesis of marasmic acid (1), an antimicrobial sesquiterpene, has been achieved in a stereoselective manner from known enone 9. The initial key step involves stereo-and regioselective photocycloaddition of aliene to enone 8. The most important strategic transformation in this synthesis is the acid-catalyzed rearrangement of 1-oxaspirohexane 7 to lactone 6 having a norcarane skeleton with an appendage suitable for further manipulation. Finally, Sharpless allylic oxidation followed by Swern oxidation of hydroxy ester 24 provided a route to methyl marasmate (5).

AB - A formal total synthesis of marasmic acid (1), an antimicrobial sesquiterpene, has been achieved in a stereoselective manner from known enone 9. The initial key step involves stereo-and regioselective photocycloaddition of aliene to enone 8. The most important strategic transformation in this synthesis is the acid-catalyzed rearrangement of 1-oxaspirohexane 7 to lactone 6 having a norcarane skeleton with an appendage suitable for further manipulation. Finally, Sharpless allylic oxidation followed by Swern oxidation of hydroxy ester 24 provided a route to methyl marasmate (5).

UR - http://www.scopus.com/inward/record.url?scp=0025285248&partnerID=8YFLogxK

U2 - 10.1021/ja00158a042

DO - 10.1021/ja00158a042

M3 - Article

AN - SCOPUS:0025285248

VL - 112

SP - 775

EP - 779

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 2

ER -

Synthesis of (±)-Marasmic Acid via 1-Oxaspirohexane Rearrangement

摘要

存取文件

其它文件與鏈接

指紋

引用此