Chemistry of spectinomycin: its total synthesis, stereocontrolled rearrangement, and analogs

1985 ◽  
Vol 63 (1) ◽  
pp. 163-172 ◽  
Author(s):  
Stephen Hanessian ◽  
René Roy
Keyword(s):  
Total Synthesis ◽  
Stereocontrolled Synthesis ◽  
Chemical Correlation

The total stereocontrolled synthesis of the antibiotic spectinomycin is described, based on the regiospecific functionalization and manipulation of appropriate starting materials. The tertiary ketol rearrangement of the antibiotic and its derivatives was studied and the stereochemical identity of spectinoic acid was established by chemical correlation. Dihydrospectinomycin derivatives undergo unusual solvolysis reactions.

Total synthesis of (+)-pederin. 1. Stereocontrolled synthesis of (+)-benzoylpedamide

1985 ◽  
Vol 26 (52) ◽  
pp. 6461-6464 ◽  
Author(s):  
Tadashi Nakata ◽  
Shigeto Nagao ◽  
Nobuyuki Mori ◽  
Takeshi Oishi
Keyword(s):  
Total Synthesis ◽  
Stereocontrolled Synthesis

scholarly journals Stereocontrolled Synthesis of Adjacent Acyclic Quaternary-Tertiary Motifs: Application to a Concise Total Synthesis of (−)-Filiformin

2014 ◽  
Vol 53 (22) ◽  
pp. 5552-5555 ◽  
Author(s):  
Daniel J. Blair ◽  
Catherine J. Fletcher ◽  
Katherine M. P. Wheelhouse ◽  
Varinder K. Aggarwal
Keyword(s):  
Total Synthesis ◽  
Stereocontrolled Synthesis

Total synthesis of the polyether antibiotic lysocellin. 1. Stereocontrolled synthesis of the C1-C9 and C16-C23 fragments

1992 ◽  
Vol 33 (38) ◽  
pp. 5537-5540 ◽  
Author(s):  
Kiyoshi Horita ◽  
Takayuki Inoue ◽  
Kazuhiro Tanaka ◽  
Osamu Yonemitsu
Keyword(s):  
Total Synthesis ◽  
Stereocontrolled Synthesis

The total synthesis of swinholide A. Part 3: A stereocontrolled synthesis of (−)-pre-swinholide A.

Tetrahedron ◽  
1995 ◽  
Vol 51 (34) ◽  
pp. 9437-9466 ◽  
Author(s):  
Ian Paterson ◽  
Richard A. Ward ◽  
Julian D. Smith ◽  
John G. Cumming ◽  
Kap-Sun Yeung
Keyword(s):  
Total Synthesis ◽  
Stereocontrolled Synthesis ◽  
Swinholide A

14-Step Synthesis of (+)-Ingenol from (+)-3-Carene

Science ◽  
2013 ◽  
Vol 341 (6148) ◽  
pp. 878-882 ◽  
Author(s):  
Lars Jørgensen ◽  
Steven J. McKerrall ◽  
Christian A. Kuttruff ◽  
Felix Ungeheuer ◽  
Jakob Felding ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Anticancer Activity ◽  
Actinic Keratosis ◽  
Skin Condition ◽  
Chemical Production ◽  
Two Phase ◽  
Chemical Complexity ◽  
Euphorbia Peplus ◽  
Stereocontrolled Synthesis ◽  
Phase Design

Ingenol is a diterpenoid with unique architecture and has derivatives possessing important anticancer activity, including the recently Food and Drug Administration–approved Picato, a first-in-class drug for the treatment of the precancerous skin condition actinic keratosis. Currently, that compound is sourced inefficiently from Euphorbia peplus. Here, we detail an efficient, highly stereocontrolled synthesis of (+)-ingenol proceeding in only 14 steps from inexpensive (+)-3-carene and using a two-phase design. This synthesis will allow for the creation of fully synthetic analogs of bioactive ingenanes to address pharmacological limitations and provides a strategic blueprint for chemical production. These results validate two-phase terpene total synthesis as not only an academic curiosity but also a viable alternative to isolation or bioengineering for the efficient preparation of polyoxygenated terpenoids at the limits of chemical complexity.

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