Pectenotoxin-2 Synthetic Studies. 3. Assessment of the Capacity for Stereocontrolled Cyclization To Form the Entire C1−C26 Subunit Based upon the Double Bond Geometry Across C15-C16

2007 ◽  
Vol 72 (5) ◽  
pp. 1747-1754 ◽  
Author(s):  
Patrick D. O'Connor ◽  
Christopher K. Knight ◽  
Dirk Friedrich ◽  
Xiaowen Peng ◽  
Leo A. Paquette
Keyword(s):  
Double Bond ◽  
Synthetic Studies ◽  
Pectenotoxin 2

Synthetic Studies Toward Pectenotoxin 2. Part I. Stereocontrolled Access to the C10−C22Fragment

2008 ◽  
Vol 10 (19) ◽  
pp. 4179-4182 ◽  
Author(s):  
Jatta E. Aho ◽  
Elina Salomäki ◽  
Kari Rissanen ◽  
Petri M. Pihko
Keyword(s):  
Synthetic Studies ◽  
Pectenotoxin 2

ChemInform Abstract: Synthetic Studies Toward Pectenotoxin 2. Part 1. Stereocontrolled Access to the C10-C22Fragment.

ChemInform ◽  
2009 ◽  
Vol 40 (6) ◽  
Author(s):  
Jatta E. Aho ◽  
Elina Salomaeki ◽  
Kari Rissanen ◽  
Petri M. Pihko
Keyword(s):  
Synthetic Studies ◽  
Pectenotoxin 2

Synthetic Studies in the Veratrum Alkaloid Series. II. The Total Synthesis of Verarine, Veratramine, Jervine, and Veratrobasine

1975 ◽  
Vol 53 (12) ◽  
pp. 1796-1817 ◽  
Author(s):  
James P. Kutney ◽  
John Cable ◽  
William A. F. Gladstone ◽  
Harald W. Hanssen ◽  
G. Vijay Nair ◽  
...  
Keyword(s):  
Natural Products ◽  
Double Bond ◽  
Total Synthesis ◽  
Similar Sequence ◽  
Synthetic Studies ◽  
Subsequent Introduction ◽  
Methyl Pyridine

Coupling of 3β-acetoxy-5α-etiojerv-12(13)-en-17-one (1) with the lithio derivative of 2-ethyl-5-methylpyridine provides the crucial intermediate (3) for the subsequent elaboration to verarine. Aromatization of 3 to 4 and reduction of the latter provides a mixture from which N-acetyl-5α,6-dihydroverarine (11) was isolated. Subsequent introduction of the 5,6-double bond in the latter and removal of the N-acetate function completed the synthesis of verarine (31). In a similar sequence of reactions employing 1 and the lithio derivative of 2-ethyl-3-methoxy-5-methyl-pyridine, the resultant intermediate (54), was elaborated to 5α,6-dihydroveratramine (56). Due to known conversions of the latter to veratramine (14), jervine (32), veratrobasine (33), and 11-deoxojervine (34), the formal total synthesis of these natural products is complete.

Synthetic Studies towards Pectenotoxin-2: Synthesis of the Nonanomeric 10-epi-ABCDE Ring Segment by Kinetic Spiroketalization

2011 ◽  
Vol 2011 (9) ◽  
pp. 1682-1694 ◽  
Author(s):  
Jatta E. Aho ◽  
Antti Piisola ◽  
K. Syam Krishnan ◽  
Petri M. Pihko
Keyword(s):  
Ring Segment ◽  
Synthetic Studies ◽  
Pectenotoxin 2

Synthetic Studies Toward Pectenotoxin 2. Part II. Synthesis of the CDE and CDEF Ring Systems

2008 ◽  
Vol 10 (19) ◽  
pp. 4183-4185 ◽  
Author(s):  
Hannes Helmboldt ◽  
Jatta E. Aho ◽  
Petri M. Pihko
Keyword(s):  
Ring Systems ◽  
Synthetic Studies ◽  
Pectenotoxin 2

Pectenotoxin-2 Synthetic Studies. 2. Construction and Conjoining of ABC and DE Eastern Hemisphere Subtargets

2005 ◽  
Vol 7 (9) ◽  
pp. 1813-1816 ◽  
Author(s):  
Dmitriy Bondar ◽  
Jian Liu ◽  
Thomas Müller ◽  
Leo A. Paquette
Keyword(s):  
Eastern Hemisphere ◽  
Synthetic Studies ◽  
Pectenotoxin 2

scholarly journals Synthetic studies towards d-modified paclitaxel analogues

2012 ◽  
Vol 77 (11) ◽  
pp. 1529-1539
Author(s):  
Zorana Ferjancic ◽  
Radomir Matovic ◽  
Radomir Saicic
Keyword(s):  
Double Bond ◽  
Hydroxy Group ◽  
Oxidative Cleavage ◽  
Protecting Group ◽  
Terminal Double Bond ◽  
Synthetic Sequence ◽  
Sterically Hindered ◽  
Synthetic Studies

A synthetic sequence has been developed for the preparation of 9,10-O-diacetyl-4-desmethylene-4?-(3-butenyl)-4?-hydroxy-5-O-mesyltaxicin I-1,2-carbonate 3, an intermediate in the attempted synthesis of cyclobutane paclitaxel analogue. A series of reactions of 3 has been investigated, including the protection of sterically hindered C-4? hydroxy group and oxidative cleavage of the terminal double bond. Cyclization of 13 to the cyclobutane-containing intermediate failed due to unexpected instability of the DMS protecting group under basic conditions.

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