Enantioselective [4 + 2] Cycloadditions ofo-Quinone Methides:  Total Synthesis of (+)-Mimosifoliol and Formal Synthesis of (+)-Tolterodine

2004 ◽  
Vol 69 (26) ◽  
pp. 9196-9203 ◽  
Author(s):  
Carolyn Selenski ◽  
Thomas R. R. Pettus
Keyword(s):  
Total Synthesis ◽  
Quinone Methides ◽  
Formal Synthesis

Chemoenzymatic Formal Total Synthesis of Pancratistatin from Narciclasine-Type Compounds via Myers Transposition: Model Study for a Short Conversion of Narciclasine to Pancratistatin

Synlett ◽  
2017 ◽  
Vol 28 (20) ◽  
pp. 2896-2900 ◽  
Author(s):  
Ringaile Lapinskaite ◽  
Mukund Ghavre ◽  
Chelsea Rintelmann ◽  
Korey Bedard ◽  
Helen Dela Paz ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Recombinant Strain ◽  
Optical Purity ◽  
Allylic Alcohol ◽  
Formal Synthesis ◽  
Toluene Dioxygenase ◽  
Single Isomer ◽  
Model Study ◽  
New Compounds ◽  
Subsequent Opening

A formal total synthesis of pancratistatin was accomplished by conversion of advanced intermediates, used in the synthesis of narciclasine, to pancratistatin precursors via Myers’ reductive transposition as the key strategic step. The synthesis began with the whole cell fermentation of m-dibromobenzene with JM109(pDTG601a), a recombinant strain that over-expresses toluene dioxygenase, which provided the corresponding cis-dihydrodiol 16 as a single isomer with complete optical purity. The key reductive transposition of the allylic alcohol 8a to olefin 9a allowed for further installation of the C-1/C-2 trans-diol, ­required for the pancratistatin scaffold, through the introduction of a cyclic sulfate and its subsequent opening. The formal synthesis of pancratistatin was accomplished in 14 steps (12 operations) from commercially available m-dibromobenzene. Experimental and spectral data are provided for all new compounds.

scholarly journals Expedient Access to Enantiopure Cyclopentanic Natural Products: Total Synthesis of (-)-Cyclonerodiol

2015 ◽  
Vol 10 (1) ◽  
pp. 1934578X1501000
Author(s):  
Carmen Pérez Morales ◽  
M. Mar Herrador ◽  
José F. Quílez del Moral ◽  
Alejandro F. Barrero
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Radical Cyclization ◽  
Formal Synthesis ◽  
Common Precursor ◽  
Enantiospecific Synthesis ◽  
Optically Pure

Following the principles of collective total synthesis, a number of natural products sharing an optically pure, multifunctional, cyclopentanic core were synthesized from a common precursor: plinol A (1). This intermediate was efficiently obtained in only four steps from (-)-linalool (2) using as the key step a Ti(III)-mediated diastereoselective radical cyclization. The feasibility of this approach was confirmed with the expedient enantiospecific synthesis of cyclonerodiol (3), and the formal synthesis of chocol G (4) and piperitone (5).

Synthesis of Polyprenylated Acylphloroglucinols Using Bridgehead Lithiation:  The Total Synthesis of Racemic Clusianone and a Formal Synthesis of Racemic Garsubellin A

2007 ◽  
Vol 72 (13) ◽  
pp. 4803-4815 ◽  
Author(s):  
Nadia M. Ahmad ◽  
Vincent Rodeschini ◽  
Nigel S. Simpkins ◽  
Simon E. Ward ◽  
Alexander J. Blake
Keyword(s):  
Total Synthesis ◽  
Formal Synthesis

scholarly journals Catalytic Selective Cyclizations of Aminocyclopropanes: Formal Synthesis of Aspidospermidine and Total Synthesis of Goniomitine

2010 ◽  
Vol 122 (33) ◽  
pp. 5903-5906 ◽  
Author(s):  
Filippo De Simone ◽  
Jürg Gertsch ◽  
Jérôme Waser
Keyword(s):  
Total Synthesis ◽  
Formal Synthesis

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.

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