Abstract
Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 4338-4341 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 14 |
| Issue number | 17 |
| DOIs | |
| State | Published - Sep 7 2012 |
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ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
- Biochemistry
Cite this
Synthesis of 6,6′-binaphthopyran-2-one natural products : Pigmentosin A, talaroderxines A and B. / Grove, Charles I.; Di Maso, Michael J.; Jaipuri, Firoz A.; Kim, Michelle B.; Shaw, Jared T.
In: Organic Letters, Vol. 14, No. 17, 07.09.2012, p. 4338-4341.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis of 6,6′-binaphthopyran-2-one natural products
T2 - Pigmentosin A, talaroderxines A and B
AU - Grove, Charles I.
AU - Di Maso, Michael J.
AU - Jaipuri, Firoz A.
AU - Kim, Michelle B.
AU - Shaw, Jared T.
PY - 2012/9/7
Y1 - 2012/9/7
N2 - Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin.
AB - Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin.
UR - http://www.scopus.com/inward/record.url?scp=84866024108&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84866024108&partnerID=8YFLogxK
U2 - 10.1021/ol301743t
DO - 10.1021/ol301743t
M3 - Article
C2 - 22889083
AN - SCOPUS:84866024108
VL - 14
SP - 4338
EP - 4341
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 17
ER -