Chapman's (O. L. Chapman, then at Iowa State and later at UCLA) classic total synthe- sis of (+)-carpanone is so remarkably simple that it is used as an undergraduate labora- tory preparation. It is modeled on a possible biosynthetic route for this lignan-derived natural product. Phenol oxidations figure prominently in many such biosyntheses of natural products. In one step, this reaction creates no less than five contiguous chiral centers, all in the correct relative configuration. K* tert-Buo- DMSO ОН HO. [0] (+)-Carpanone

Chapman's (O. L. Chapman, then at Iowa State and later at UCLA) classic total synthe- sis of (+)-carpanone is so remarkably simple that it is used as an undergraduate labora- tory preparation. It is modeled on a possible biosynthetic route for this lignan-derived natural product. Phenol oxidations figure prominently in many such biosyntheses of natural products. In one step, this reaction creates no less than five contiguous chiral centers, all in the correct relative configuration. K* tert-Buo- DMSO ОН HO. [0] (+)-Carpanone

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter24: Catalytic Carbon-carbon Bond Formation

Section: Chapter Questions

Problem 24.36P

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Over the past several decades, chemists have developed a number of synthetic methodologies for the synthesis of steroid hormones. One of these, developed by Lutz Tietze at the Institut für Organische Chemie der Georg-August-Universität, Göttingen, Germany, used a double Heck reaction to create ring B of the steroid nucleus. As shown in the following retrosynthetic analysis, a key intermediate in his synthesis is compound (1). Two Heck reaction disconnects of this intermediate give compounds (2) and (3). Compound (2) contains the aromatic ring that becomes ring A of estrone. Compound (3) contains the fused five- and six-membered rings that become rings C and D of estrone. Q.Propose structural formulas for compounds (2) and (3).
Over the past several decades, chemists have developed a number of synthetic methodologies for the synthesis of steroid hormones. One of these, developed by Lutz Tietze at the Institut für Organische Chemie der Georg-August-Universität, Göttingen, Germany, used a double Heck reaction to create ring B of the steroid nucleus. As shown in the following retrosynthetic analysis, a key intermediate in his synthesis is compound (1). Two Heck reaction disconnects of this intermediate give compounds (2) and (3). Compound (2) contains the aromatic ring that becomes ring A of estrone. Compound (3) contains the fused five- and six-membered rings that become rings C and D of estrone. Q.Name the types of functional groups in estrone
Over the past several decades, chemists have developed a number of synthetic methodologies for the synthesis of steroid hormones. One of these, developed by Lutz Tietze at the Institut für Organische Chemie der Georg-August-Universität, Göttingen, Germany, used a double Heck reaction to create ring B of the steroid nucleus. As shown in the following retrosynthetic analysis, a key intermediate in his synthesis is compound (1). Two Heck reaction disconnects of this intermediate give compounds (2) and (3). Compound (2) contains the aromatic ring that becomes ring A of estrone. Compound (3) contains the fused five- and six-membered rings that become rings C and D of estrone. Q.How many chiral centers are present in estrone?
Over the past several decades, chemists have developed a number of synthetic methodologies for the synthesis of steroid hormones. One of these, developed by Lutz Tietze at the Institut für Organische Chemie der Georg-August-Universität, Göttingen, Germany, used a double Heck reaction to create ring B of the steroid nucleus. As shown in the following retrosynthetic analysis, a key intermediate in his synthesis is compound (1). Two Heck reaction disconnects of this intermediate give compounds (2) and (3). Compound (2) contains the aromatic ring that becomes ring A of estrone. Compound (3) contains the fused five- and six-membered rings that become rings C and D of estrone. Q.Show how your proposals for compounds (2) and (3) can be converted to compound (1). (Note: In the course of developing this synthesis, Tietze discovered that vinylic bromides and iodides are more reactive in Heck reactions than are aryl bromides and iodides.)
Over the past several decades, chemists have developed a number of synthetic methodologies for the synthesis of steroid hormones. One of these, developed by Lutz Tietze at the Institut für Organische Chemie der Georg-August-Universität, Göttingen, Germany, used a double Heck reaction to create ring B of the steroid nucleus. As shown in the following retrosynthetic analysis, a key intermediate in his synthesis is compound (1). Two Heck reaction disconnects of this intermediate give compounds (2) and (3). Compound (2) contains the aromatic ring that becomes ring A of estrone. Compound (3) contains the fused five- and six-membered rings that become rings C and D of estrone. Q. In the course of the double Heck reactions, two new chiral centers are created. Assume in compound (3), the precursor to rings C and D of estrone, that the fusion of rings C and D is trans and that the angular methyl group is above the plane of the ring. Given this stereochemistry, predict the stereochemistry of…
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