Asymmetric Reductive Cyclization. Total Synthesis of (−)-C10-Desmethyl Arteannuin B

1996 ◽  
Vol 61 (10) ◽  
pp. 3240-3244 ◽  
Author(s):  
Michael Schwaebe ◽  
R. Daniel Little
Keyword(s):  
Total Synthesis ◽  
Reductive Cyclization

ChemInform Abstract: Formal Total Synthesis of (-)-Dendrobine Using Zirconium-Promoted Reductive Cyclization.

ChemInform ◽  
2010 ◽  
Vol 26 (14) ◽  
pp. no-no
Author(s):  
N. UESAKA ◽  
F. SAITOH ◽  
M. MORI ◽  
M. SHIBASAKI ◽  
K. OKAMURA ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Reductive Cyclization

The Catalytic Alkylative Desymmetrization of Anhydrides in a Formal Synthesis of Ionomycin

Synthesis ◽  
2018 ◽  
Vol 50 (22) ◽  
pp. 4343-4350
Author(s):  
Tomislav Rovis ◽  
Kevin Oberg ◽  
Brian Cochran ◽  
Matthew Cook
Keyword(s):  
Total Synthesis ◽  
Reductive Cyclization ◽  
Formal Synthesis

The catalytic desymmetrization of anhydrides with zinc reagents provides access to deoxypolypropionate and polypropionate synthons. A synthesis of ionomycin was pursued in which three of the four fragments were assembled using this methodology. Two of the strategies (enol silane/oxocarbenium coupling and reductive cyclization) were not successful at installing the C23 stereocenter, but this stereochemical issue was overcome through a reduction/SN2 approach. In addition to the synthesis of a protected diastereomer of ionomycin, the synthesis of a C17–C32 fragment constitutes a formal total synthesis.

ChemInform Abstract: Total Synthesis of Rutaecarpine and Analogues by Tandem Azido Reductive Cyclization Assisted by Microwave Irradiation.

ChemInform ◽  
2011 ◽  
Vol 42 (19) ◽  
pp. no-no
Author(s):  
Ahmed Kamal ◽  
M. Kashi Reddy ◽  
T. Srinivasa Reddy ◽  
Leonardo Silva Santos ◽  
Nagula Shankaraiah
Keyword(s):  
Microwave Irradiation ◽  
Total Synthesis ◽  
Reductive Cyclization

A regioselective facile synthesis of furo[3,4-b]carbazolones: application to the total synthesis of mafaicheenamine E and claulansine D

2015 ◽  
Vol 13 (22) ◽  
pp. 6344-6352 ◽  
Author(s):  
Dipakranjan Mal ◽  
Joyeeta Roy
Keyword(s):  
Total Synthesis ◽  
Reductive Cyclization ◽  
Facile Synthesis

1-Hydroxycarbazole-2,3-dicarboxylates have been shown to undergo chemoselective reductive cyclization to furo[3,4-b]carbazolones with LiAlH4.

The total synthesis of (+)-ryanodol. Part IV. Preparation of (+)-ryanodol from (+)-anhydroryanodol

1990 ◽  
Vol 68 (1) ◽  
pp. 186-192 ◽  
Author(s):  
Pierre Deslongchamps ◽  
André Bélanger ◽  
Daniel J. F. Berney ◽  
Hans-Jürg Borschberg ◽  
Robert Brousseau ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Reductive Cyclization

This paper reports the transformation of (+)-anhydroryanodol (6) to (+)-ryanodol (7) by reductive cyclization of lactone epoxide derivatives 9 and 20 (Scheme 4). Keywords: anhydroryanodol, ryanodol, diterpene, synthesis, reductive cyclization.

scholarly journals Total Synthesis of the Galbulimima Alkaloid (±)-GB 13

2010 ◽  
Vol 63 (5) ◽  
pp. 742 ◽  
Author(s):  
Matthew M. W. McLachlan ◽  
Patrick D. O'Connor ◽  
Kelly A. Fairweather ◽  
Anthony C. Willis ◽  
Lewis N. Mander
Keyword(s):  
Total Synthesis ◽  
Liquid Ammonia ◽  
Forest Tree ◽  
Alder Reaction ◽  
Diels Alder ◽  
Piperidine Ring ◽  
Reductive Cyclization ◽  
The North ◽  
Diels Alder Reaction ◽  
Acid Catalyzed

The synthesis of alkaloid GB 13 (4), isolated from the North Australian rain forest tree Galbulimima belgraveana is described. Birch reductive alkylation of 2,5-dimethoxybenzoic acid by 3-methoxybenzyl bromide, followed by an acid-catalyzed cyclization was used to synthesize the [3.3.1]bicyclononane 12. Ring contraction performed on the diazoketone 19 followed by a Diels–Alder reaction generated a pentacyclic intermediate 34 with a carbon skeleton closely resembling the target alkaloid. The surplus nitrile substituent, required for activation and regioselectivity in the Diels–Alder reaction, was removed by treatment with lithium and liquid ammonia. Birch reduction of the aromatic ring could be performed at the same time to give diene 38 and thence enone 41, which was cleaved by means of an Eschenmoser fragmentation. The piperidine ring found in the natural product was formed by reductive cyclization of bis-oxime 49 derived from the alkynyl ketone 48 and the resulting material further elaborated to GB 13.

A Total Synthesis of (±)-Ceratopicanol via Palladium Catalyzed Reductive Cyclization

2020 ◽  
Vol 2020 (31) ◽  
pp. 4931-4936
Author(s):  
Rira Kim ◽  
Sanghyeon Lee ◽  
Jaeyeon Lee ◽  
Hee-Yoon Lee
Keyword(s):  
Total Synthesis ◽  
Reductive Cyclization ◽  
Palladium Catalyzed
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