Chiral synthesis of polyketide-derived natural products. 28. Synthesis of 16-membered macrolide aglycons, carbonolide A, leuconolides, and maridonolides, via carbonolide B type compounds by virtue of completely stereoselective epoxidation and reduction based on the conformational control of macrolide rings with protecting groups

Noriyuki Nakajima; Kouichi Uoto; Tomohiro Matsushima; Osamu Yonemitsu; Hitoshi Goto; Eiji Osawa

doi:10.1021/jo00291a002

Chiral synthesis of polyketide-derived natural products. 28. Synthesis of 16-membered macrolide aglycons, carbonolide A, leuconolides, and maridonolides, via carbonolide B type compounds by virtue of completely stereoselective epoxidation and reduction based on the conformational control of macrolide rings with protecting groups

The Journal of Organic Chemistry ◽

10.1021/jo00291a002 ◽

1990 ◽

Vol 55 (4) ◽

pp. 1129-1132 ◽

Cited By ~ 9

Author(s):

Noriyuki Nakajima ◽

Kouichi Uoto ◽

Tomohiro Matsushima ◽

Osamu Yonemitsu ◽

Hitoshi Goto ◽

...

Keyword(s):

Natural Products ◽

Protecting Groups ◽

Conformational Control ◽

Chiral Synthesis ◽

Stereoselective Epoxidation ◽

Carbonolide B

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ChemInform Abstract: Chiral Synthesis of Nitrogenous Natural Products Based on Nonchelation Conformational Control

ChemInform ◽

10.1002/chin.199606319 ◽

2010 ◽

Vol 27 (6) ◽

pp. no-no

Author(s):

C. KIBAYASHI

Keyword(s):

Natural Products ◽

Conformational Control ◽

Chiral Synthesis

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ChemInform Abstract: Chiral Synthesis of Polyketide-Derived Natural Products. Part 29. A Stereocontrolled Synthesis of the 16-Membered Ring Macrolide Aglycones, Niddanolide, Carbonolide B, and Platenonolide W1.

ChemInform ◽

10.1002/chin.199031309 ◽

1990 ◽

Vol 21 (31) ◽

Author(s):

N. NAKAJIMA ◽

K. UOTO ◽

O. YONEMITSU

Keyword(s):

Natural Products ◽

Membered Ring ◽

Chiral Synthesis ◽

Stereocontrolled Synthesis ◽

Carbonolide B

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ChemInform Abstract: Chiral Synthesis of Polyketide-Derived Natural Products. Part 34. Facile Total Synthesis of Carbonolides by Wittig-Horner Macrocyclization and Stereoselective Epoxidation.

ChemInform ◽

10.1002/chin.199143166 ◽

2010 ◽

Vol 22 (43) ◽

pp. no-no

Author(s):

N. NAKAJIMA ◽

K. UOTO ◽

O. YONEMITSU ◽

T. HATA

Keyword(s):

Natural Products ◽

Total Synthesis ◽

Chiral Synthesis ◽

Stereoselective Epoxidation

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Chiral Synthesis of Nitrogenous Natural Products Based on Nonchelation Conformational Control.

Journal of Synthetic Organic Chemistry Japan ◽

10.5059/yukigoseikyokaishi.53.700 ◽

1995 ◽

Vol 53 (8) ◽

pp. 700-711 ◽

Cited By ~ 2

Author(s):

Chihiro KIBAYASHI

Keyword(s):

Natural Products ◽

Conformational Control ◽

Chiral Synthesis

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CONFORMATIONAL CONTROL IN NATURAL PRODUCTS SYNTHESIS

Chemistry for the Future ◽

10.1016/b978-0-08-029249-6.50029-5 ◽

1984 ◽

pp. 199-209

Author(s):

W. Clark Still ◽

Cesare Gennari ◽

Jose A. Noguez

Keyword(s):

Natural Products ◽

Conformational Control ◽

Natural Products Synthesis

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ChemInform Abstract: CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL PRODUCTS. PART 4. SYNTHESIS OF F A LEFT-HAND SEGMENT WITH SIX CONSECUTIVE CHIRAL CENTERS OF DIHYDROERYTHRONOLIDE A FOR THE TOTAL SYNTHESIS OF ERYTHROMYCIN A FROM D-GLUCOSE

Chemischer Informationsdienst ◽

10.1002/chin.198517313 ◽

1985 ◽

Vol 16 (17) ◽

Author(s):

Y. OIKAWA ◽

T. NISHI ◽

O. YONEMITSU

Keyword(s):

Natural Products ◽

Total Synthesis ◽

Chiral Synthesis ◽

Left Hand ◽

Chiral Centers ◽

Erythromycin A

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Chiral synthesis of polyketide-derived natural products. Part 6. Chemical correlation of chiral synthons, derived from D-glucose for the synthesis of erythromycin A, with chemical cleavage products the natural antibiotic

Journal of the Chemical Society Perkin Transactions 1 ◽

10.1039/p19850000027 ◽

1985 ◽

pp. 27 ◽

Cited By ~ 2

Author(s):

Yuji Oikawa ◽

Takao Nishi ◽

Osamu Yonemitsu

Keyword(s):

Natural Products ◽

Chiral Synthesis ◽

Chemical Cleavage ◽

Chemical Correlation ◽

Erythromycin A

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Protecting-group-free synthesis of haterumadienone- and puupehenone-type marine natural products

Green Chemistry ◽

10.1039/c7gc00704c ◽

2017 ◽

Vol 19 (9) ◽

pp. 2140-2144 ◽

Cited By ~ 12

Author(s):

Hong-Shuang Wang ◽

Hui-Jing Li ◽

Jun-Li Wang ◽

Yan-Chao Wu

Keyword(s):

Natural Products ◽

Transition Metals ◽

Marine Natural Products ◽

Protecting Groups ◽

Protecting Group

The atom- and step-economical synthesis of seven puupehenone- and haterumadienone-type marine natural products without the use of protecting groups and transition metals has been achieved from the abundant feedstock chemical sclareolide in only 6 to 9 steps.

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ChemInform Abstract: CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL PRODUCTS. PART 5. SYNTHESIS OF F A CHIRAL SEGMENT CORRESPONDING TO THE C-1-C-5 UNIT OF ERYTHROMYCIN A FROM D-GLUCOSE

Chemischer Informationsdienst ◽

10.1002/chin.198517314 ◽

1985 ◽

Vol 16 (17) ◽

Author(s):

Y. OIKAWA ◽

T. NISHI ◽

O. YONEMITSU

Keyword(s):

Natural Products ◽

Chiral Synthesis ◽

Erythromycin A

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Chiral synthesis of polyketide-derived natural products. 44. Large Laboratory scale Synthesis of (2S,3S)-2-(4-Methoxybenzyloxy)-3,4-O-(3-pentylidene)-1,3,4-butantriol, a Versatile Chiral Building Block in Natural Product Synthesis.

Chemical and Pharmaceutical Bulletin ◽

10.1248/cpb.42.683 ◽

1994 ◽

Vol 42 (3) ◽

pp. 683-685 ◽

Cited By ~ 4

Author(s):

Kiyoshi HORITA ◽

Youji SAKURAI ◽

Shun-ichiro HACHIYA ◽

Masaaki NAGASAWA ◽

Osamu YONEMITSU

Keyword(s):

Natural Products ◽

Natural Product ◽

Building Block ◽

Laboratory Scale ◽

Natural Product Synthesis ◽

Chiral Synthesis ◽

Chiral Building Block

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