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Literature DB >> 21309525

A short asymmetric route to the bromophycolide A and D skeleton.

Hongkun Lin¹, Susan S Pochapsky, Isaac J Krauss.

Abstract

An asymmetric synthesis of the bromophycolide D ring system has been achieved in seven steps from a known geranylgeranylated benzoate, via bromonium-promoted transannular cyclization of a macrocyclic intermediate.

Entities: Chemical Disease Mutation Species

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Year: 2011 PMID： 21309525 PMCID： PMC3065244 DOI： 10.1021/ol200099n

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

13 in total

Review 1. A case study in biomimetic total synthesis: polyolefin carbocyclizations to terpenes and steroids.

Authors: Ryan A Yoder; Jeffrey N Johnston
Journal: Chem Rev Date: 2005-12 Impact factor: 60.622

2. Bromophycolides C-I from the Fijian red alga Callophycus serratus.

Authors: Julia Kubanek; Anne C Prusak; Terry W Snell; Rachel A Giese; Craig R Fairchild; William Aalbersberg; Mark E Hay
Journal: J Nat Prod Date: 2006-05 Impact factor: 4.050

3. Bioactive bromophycolides R-U from the Fijian red alga Callophycus serratus.

Authors: An-Shen Lin; E Paige Stout; Jacques Prudhomme; Karine Le Roch; Craig R Fairchild; Scott G Franzblau; William Aalbersberg; Mark E Hay; Julia Kubanek
Journal: J Nat Prod Date: 2010-02-26 Impact factor: 4.050

4. Highly effective transition structure designed catalyst for the enantio- and position-selective dihydroxylation of polyisoprenoids.

Authors: E J Corey; J Zhang
Journal: Org Lett Date: 2001-10-04 Impact factor: 6.005

2. Relay Cross Metathesis for the Iterative Construction of Terpenoids and Synthesis of a Diterpene-Benzoate Macrolide of Biogenetic Relevance to the Bromophycolides.

Authors: Karim A Bahou; D Christopher Braddock; Adam G Meyer; G Paul Savage
Journal: Org Lett Date: 2020-03-31 Impact factor: 6.005

2 in total

A short asymmetric route to the bromophycolide A and D skeleton.

Review 1. A case study in biomimetic total synthesis: polyolefin carbocyclizations to terpenes and steroids.

2. Bromophycolides C-I from the Fijian red alga Callophycus serratus.

3. Bioactive bromophycolides R-U from the Fijian red alga Callophycus serratus.

4. Highly effective transition structure designed catalyst for the enantio- and position-selective dihydroxylation of polyisoprenoids.

5. Simple reagents for direct halonium-induced polyene cyclizations.

6. Antineoplastic diterpene-benzoate macrolides from the Fijian red alga Callophycus serratus.

7. Enantioselective halocyclization of polyprenoids induced by nucleophilic phosphoramidites.

8. On the absolute configurational stability of bromonium and chloronium ions.

9. Antimalarial bromophycolides J-Q from the Fijian red alga Callophycus serratus.

10. Synthesis of lactones using substituted benzoic anhydride as a coupling reagent.

Review 1. Stereoselective Halogenation in Natural Product Synthesis.

2. Relay Cross Metathesis for the Iterative Construction of Terpenoids and Synthesis of a Diterpene-Benzoate Macrolide of Biogenetic Relevance to the Bromophycolides.