Biomimetic Synthesis of Hyperjapones F-I

2018 ◽  
Vol 71 (9) ◽  
pp. 649 ◽  
Author(s):  
Hiu C. Lam ◽  
Quang D. Phan ◽  
Christopher J. Sumby ◽  
Jonathan H. George
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Diels Alder ◽  
Biomimetic Synthesis ◽  
Enantiomerically Pure ◽  
Biosynthetic Precursor ◽  
Hypericum Japonicum ◽  
Optical Rotations

Hyperjapones F–I are tetracyclic meroterpenoids recently isolated from Hypericum japonicum. All four of these natural products have been synthesised using oxidative, intermolecular hetero-Diels–Alder reactions to couple their common biosynthetic precursor, norflavesone, to the appropriate monoterpene building blocks: sabinene, β-pinene, and α-pinene. The synthesis of enantiomerically pure hyperjapones H and I and comparison of their optical rotations to those of the natural samples indicated that these meroterpenoids are probably biosynthesised as either racemic or scalemic mixtures.

Competitive Intramolecular Diels - Alder Reactions of bis-α,β-Unsaturated Ester Derivatives of Enzymatically Derived and Enantiopure cis-1,2-Dihydrocatechols. Enantiodivergent Synthesis of Monochiral Bicyclo[2.2.2]oct-2-enes

2003 ◽  
Vol 56 (9) ◽  
pp. 861 ◽  
Author(s):  
Martin G. Banwell ◽  
Cai Chun ◽  
Alison J. Edwards ◽  
Markus M. Vögtle
Keyword(s):  
Natural Products ◽  
Single Crystal ◽  
Building Blocks ◽  
Diels Alder ◽  
Unsaturated Ester ◽  
Enantiomerically Pure ◽  
X Ray ◽  
Derivatives Of ◽  
Natural Products Synthesis

bis-Crotonate and related α,β-unsaturated ester derivatives of readily available and enantiomerically pure cis-1,2-dihydrocatechols engage, upon heating in refluxing toluene, in two competitive intramolecular Diels–Alder reactions to give varying mixtures of chromatographically separable and pseudo-enantiomeric bicyclo[2.2.2]oct-2-enes. Such adducts, many of which have been characterized by single-crystal X-ray analysis, are likely to serve as useful building blocks in natural products synthesis.

Chemoenzymatic methods for the enantioselective preparation of sesquiterpenoid natural products from aromatic precursors

2003 ◽  
Vol 75 (2-3) ◽  
pp. 223-229 ◽  
Author(s):  
M. G. Banwell ◽  
A. J. Edwards ◽  
G. J. Harfoot ◽  
K. A. Jolliffe ◽  
M. D. McLeod ◽  
...  
Keyword(s):  
Natural Products ◽  
Diels Alder ◽  
Cycloaddition Reactions ◽  
Enantiomerically Pure

The enantiomerically pure cis-1,2-dihydrocatechols 2, which are generated by enzymatic dihydroxylation of the corresponding aromatic, engage in regio- and stereo-controlled Diels-Alder cycloaddition reactions to give a range of synthetically useful bicyclo[2.2.2]octenes. Certain examples of the latter type of compound have been used as starting materials in the synthesis of the sesquiterpenoids (−)-patchoulenone and (−)-hirsutene.

ChemInform Abstract: Enzymatic Preparation of Optically Active Bicyclo(2.2.1)heptene Derivatives, Building Blocks for Terpenoid Natural Products. An Attractive Alternative to Enantioselective Diels-Alder Syntheses.

ChemInform ◽  
1989 ◽  
Vol 20 (34) ◽  
Author(s):  
J. VAN DER EYCKEN ◽  
M. VANDEWALLE ◽  
G. HEINEMANN ◽  
K. LAUMEN ◽  
M. P. SCHNEIDER ◽  
...  
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Optically Active ◽  
Diels Alder ◽  
Attractive Alternative ◽  
Enzymatic Preparation

Pigments of Fungi. LIX. Synthesis of (1S,3S)- and (1R,3R)-Austrocortilutein and (1S,3S)-Austrocortirubin from Citramalic Acid

2000 ◽  
Vol 53 (4) ◽  
pp. 245 ◽  
Author(s):  
Melvyn Gill ◽  
Michael F. Harte ◽  
Abilio Ten
Keyword(s):  
Natural Products ◽  
Diels Alder ◽  
Pure Form ◽  
Enantiomerically Pure ◽  
Naturally Occurring ◽  
First Time

The naturally occurring tetrahydroanthraquinone (1S,3S)-austrocortilutein (1) is synthesized for the first time in enantiomerically pure form by Diels–Alder cycloaddition between the functionalized butadiene derivative (8) and the chiral 1,3-dihydroxy-1,2,3,4-tetrahydro-5,8-naphthoquinone (9), the latter being derived from (R)-citramalic acid (3). The natural products (1S,3S)-austrocortirubin (2) and (1R,3R)-austrocortilutein (5) were also prepared for the first time by using the same strategy.

scholarly journals Biosynthesis and Biomimetic Synthesis of Flavonoid Diels-Alder Natural Products

2017 ◽  
Author(s):  
Shah Bakhtiar Nasir ◽  
Jia Ti Tee ◽  
Noorsaadah Abd Rahman ◽  
Chin Fei Chee
Keyword(s):  
Natural Products ◽  
Diels Alder ◽  
Biomimetic Synthesis

1998 Alfred Bader Award Lecture Tangents and targets: The synthetic highway from natural products to medicine

1999 ◽  
Vol 77 (2) ◽  
pp. 159-177 ◽  
Author(s):  
Alex G Fallis
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Diels Alder ◽  
Synthetic Studies

Synthetic studies directed toward various classes of compounds including taxoids and enediyne systems are described. These investigations include tether-controlled imtramolecular Diels-Alder reactions, carbometallation routes to dienes and furans, the use of carbohydrate building blocks, pentadienyl indium reagents for tandem cycloadditions to steroid and triterpenoid skeletons, and the synthesis of taxamycins and revolveneynes and related cyclophanes.Key words: cycloaddition, taxoids, enediyne, cyclophanes, carbometallation.

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